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Themed collection Organocatalysis

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Editorial

Organocatalysis: a web collection

Showcasing a collection of cutting edge contributions by international leaders in the field of organocatalysis.

Graphical abstract: Organocatalysis: a web collection
From the themed collection: Organocatalysis
Feature Article

Non-asymmetric organocatalysis

Organocatalytic reactions affording achiral compounds opened unexplored pathways in the synthesis of densely functionalized aromatic moieties, olefins and useful molecules such as natural substances.

Graphical abstract: Non-asymmetric organocatalysis
From the themed collection: Organocatalysis
Feature Article

Recent efforts directed to the development of more sustainable asymmetric organocatalysis

A critical discussion of recent strategies directed to the development of more sustainable asymmetric organocatalysis is presented.

Graphical abstract: Recent efforts directed to the development of more sustainable asymmetric organocatalysis
From the themed collection: Organocatalysis
Emerging Area

Asymmetric organocascades involving the formation of two C–heteroatom bonds from two distinct heteroatoms

Enantioselective organocascades creating multiple carbon–heteroatom bonds are rare but these fascinating domino processes lead to highly functionalised optically active building blocks.

Graphical abstract: Asymmetric organocascades involving the formation of two C–heteroatom bonds from two distinct heteroatoms
From the themed collection: Organocatalysis
Communication

Enantio- and periselective nitroalkene Diels–Alder reaction

It is successfully demonstrated that the nitroalkene Diels–Alder reaction can be rendered enantio- and periselective by helical–chiral hydrogen bond donor catalysts.

Graphical abstract: Enantio- and periselective nitroalkene Diels–Alder reaction
From the themed collection: Organocatalysis
Communication

Catalytic asymmetric Mannich-type reactions of α-cyano α-sulfonyl carbanions

An efficient asymmetric Mannich-type reaction of α-cyano α-sulfonyl carbanions has been achieved by exploiting the structural modularity and anion-recognition ability of chiral 1,2,3-triazolium ions. This protocol has proven to be applicable to a variety of N-Boc imines and cyanosulfones, affording β-amino α-cyanosulfones in excellent yields with high stereoselectivities.

Graphical abstract: Catalytic asymmetric Mannich-type reactions of α-cyano α-sulfonyl carbanions
From the themed collection: Organocatalysis
Communication

Catalyst-controlled reversal of chemoselectivity in acylation of 2-aminopentane-1,5-diol derivatives

An organocatalyst enables chemoselective introduction of an acyl group onto the sterically hindered secondary hydroxy group in the presence of the primary one.

Graphical abstract: Catalyst-controlled reversal of chemoselectivity in acylation of 2-aminopentane-1,5-diol derivatives
From the themed collection: Organocatalysis
Communication

Asymmetric Michael addition of boronic acids to a γ-hydroxy-α,β-unsaturated aldehyde catalyzed by resin-supported peptide

Resin-supported N-terminal prolyl peptide having suitable secondary structure effectively catalyzed asymmetric Michael addition of substituted β-styryl- and heteroarylboronates to 4-hydroxybut-2-enal.

Graphical abstract: Asymmetric Michael addition of boronic acids to a γ-hydroxy-α,β-unsaturated aldehyde catalyzed by resin-supported peptide
From the themed collection: Organocatalysis
Communication

Catalytic, enantio- and diastereoselective synthesis of γ-butyrolactones incorporating quaternary stereocentres

An organocatalyst promotes the enantio- and diastereoselective cycloaddition of aryl succinic anhydrides and aldehydes to generate paraconic acid (γ-butyrolactone) derivatives.

Graphical abstract: Catalytic, enantio- and diastereoselective synthesis of γ-butyrolactones incorporating quaternary stereocentres
From the themed collection: Organocatalysis
Communication

Synthesis of symmetric anhydrides using visible light-mediated photoredox catalysis

A new approach to anhydride formation is reported via activation of C–O bonds by the Vilsmeier–Haack reagent formed by Ru(bpy)3Cl2 and CBr4 in DMF.

Graphical abstract: Synthesis of symmetric anhydrides using visible light-mediated photoredox catalysis
From the themed collection: Organocatalysis
Communication

Enantioselective bromolactonization of cis-1,2-disubstituted olefinic acids using an amino-thiocarbamate catalyst

A facile, highly regio- and enantioselective amino-thiocarbamate-catalyzed bromolactonization of cis-1,2-disubstituted olefinic acids has been developed.

Graphical abstract: Enantioselective bromolactonization of cis-1,2-disubstituted olefinic acids using an amino-thiocarbamate catalyst
From the themed collection: Organocatalysis
Communication

Chiral proton catalysis of secondary nitroalkane additions to azomethine: synthesis of a potent GlyT1 inhibitor

Chiral proton catalysis enables an enantioselective synthesis of Lindsley's GlyT1 inhibitor and a general approach to aminomethyl azetidine pharmacophores.

Graphical abstract: Chiral proton catalysis of secondary nitroalkane additions to azomethine: synthesis of a potent GlyT1 inhibitor
From the themed collection: Organocatalysis
Communication

Enantioselective synthesis of substituted pyrans via amine-catalyzed Michael addition and subsequent enolization/cyclisation

Organocatalytic construction of pyran derivatives via amine-catalyzed Michael addition and subsequent enolization/cyclisation has been described with high enantioselectivities.

Graphical abstract: Enantioselective synthesis of substituted pyrans via amine-catalyzed Michael addition and subsequent enolization/cyclisation
From the themed collection: Organocatalysis
Communication

Envisioning an enzymatic Diels–Alder reaction by in situ acid–base catalyzed diene generation

A novel and potentially efficient enzymatic Diels–Alder reaction, involving acid–base catalysis, is presented and evaluated.

Graphical abstract: Envisioning an enzymatic Diels–Alder reaction by in situ acid–base catalyzed diene generation
From the themed collection: Organocatalysis
Communication

Trichlorosilyl triflate-mediated enantioselective directed cross-aldol reaction between ketones using a chiral phosphine oxide as an organocatalyst

The first enantioselective directed cross-aldol reaction between simple ketones using trichlorosilyl triflate and a chiral phosphine oxide catalyst is described.

Graphical abstract: Trichlorosilyl triflate-mediated enantioselective directed cross-aldol reaction between ketones using a chiral phosphine oxide as an organocatalyst
From the themed collection: Organocatalysis
Communication

Phosphine-catalyzed intramolecular γ-umpolung addition of α-aminoalkylallenic esters: facile synthesis of 3-carbethoxy-2-alkyl-3-pyrrolines

3-Carbethoxy-2-alkyl-3-pyrrolines are formed in high yields by way of phosphine-catalyzed intramolecular γ-umpolung addition of α-aminoalkylallenic esters.

Graphical abstract: Phosphine-catalyzed intramolecular γ-umpolung addition of α-aminoalkylallenic esters: facile synthesis of 3-carbethoxy-2-alkyl-3-pyrrolines
From the themed collection: Organocatalysis
Communication

Umpolung reactions in an ionic liquid catalyzed by electrogenerated N-heterocyclic carbenes. Synthesis of saturated esters from activated α,β-unsaturated aldehydes

The umpolung reaction of activated α,β-unsaturated aldehydes to saturated esters was obtained in an ionic liquid by organocatalysis of electrogenerated NHC.

Graphical abstract: Umpolung reactions in an ionic liquid catalyzed by electrogenerated N-heterocyclic carbenes. Synthesis of saturated esters from activated α,β-unsaturated aldehydes
From the themed collection: Organocatalysis
Communication

Stereoselective amine-catalyzed carbohydrate chain elongation

A highly stereoselective organocatalyzed chain elongation of carbohydrates is described.

Graphical abstract: Stereoselective amine-catalyzed carbohydrate chain elongation
From the themed collection: Organocatalysis
Communication

Enantioselective cyclopropanation of enals by oxidative N-heterocyclic carbene catalysis

α,β-Unsaturated acyl azoliums generated by oxidative carbene catalysis react stereoselectively with sulfur ylides to give cyclopropyl carboxylic esters.

Graphical abstract: Enantioselective cyclopropanation of enals by oxidative N-heterocyclic carbene catalysis
From the themed collection: Organocatalysis
Communication

Role of quaternary ammonium salts as new additives in the enantioselective organocatalytic β-benzylation of enals

Quaternary ammonium salts act as efficient neutral additives in organocatalyzed Michael additions to enals, promoting sequential iminium–enolate formation.

Graphical abstract: Role of quaternary ammonium salts as new additives in the enantioselective organocatalytic β-benzylation of enals
From the themed collection: Organocatalysis
Communication

Organocatalytic asymmetric oxy-Michael addition to a γ-hydroxy-α,β-unsaturated thioester via hemiacetal intermediates

We report an enantioselective route to β-hydroxy carboxyl compounds by asymmetric oxy-Michael addition to a γ-hydroxy-α,β-unsaturated thioester via hemiacetal intermediates.

Graphical abstract: Organocatalytic asymmetric oxy-Michael addition to a γ-hydroxy-α,β-unsaturated thioester via hemiacetal intermediates
From the themed collection: Organocatalysis
Communication

An organocatalytic Michael-aldol cascade: formal [3+2] annulation to construct enantioenriched spirocyclic oxindole derivatives

An efficient organocatalytic Michael-aldol cascade for construction of enantioenriched spirocyclic oxindoles fused with tetrahydrothiophenes was investigated.

Graphical abstract: An organocatalytic Michael-aldol cascade: formal [3+2] annulation to construct enantioenriched spirocyclic oxindole derivatives
From the themed collection: Organocatalysis
Communication

Enantioselective direct aminalization with primary carboxamides catalyzed by chiral ammonium 1,1′-binaphthyl-2,2′-disulfonates

A highly effective catalytic enantioselective direct aminal synthesis was developed. Chiral ammonium 1,1′-binaphthyl-2,2′-disulfonates, which were prepared in situ from (R)-1,1′-binaphthyl-2,2′-disulfonic acid (BINSA) and achiral amines, promoted the enantioselective addition of primary amides to aromatic aldimines.

Graphical abstract: Enantioselective direct aminalization with primary carboxamides catalyzed by chiral ammonium 1,1′-binaphthyl-2,2′-disulfonates
From the themed collection: Organocatalysis
Communication

Chiral guanidine-catalyzed asymmetric direct vinylogous Michael reaction of α,β-unsaturated γ-butyrolactams with alkylidene malonates

The asymmetric direct vinylogous reaction of α,β-unsaturated γ-butyrolactams using a C1-symmetric guanidine organocatalyst embodied a secondary amine subunit.

Graphical abstract: Chiral guanidine-catalyzed asymmetric direct vinylogous Michael reaction of α,β-unsaturated γ-butyrolactams with alkylidene malonates
From the themed collection: Organocatalysis
Communication

A highly enantioselective approach towards 2-substituted 3-bromopyrrolidines

A facile and highly enantioselective approach towards 2-substituted 3-bromopyrrolidines has been developed.

Graphical abstract: A highly enantioselective approach towards 2-substituted 3-bromopyrrolidines
From the themed collection: Organocatalysis
Communication

Direct asymmetric Mannich reaction of phthalides: facile access to chiral substituted isoquinolines and isoquinolinones

Asymmetric Mannich reaction employing phthalides has been developed for the first time, which led to stereocontrolled synthesis of 3,3-disubstituted phthalides. Facile preparation of chiral isoquinolinones and isoquinolines was also demonstrated.

Graphical abstract: Direct asymmetric Mannich reaction of phthalides: facile access to chiral substituted isoquinolines and isoquinolinones
From the themed collection: Organocatalysis
Communication

Enantioselective synthesis of optically active cis-β-thio-α-amino acid derivatives through an organocatalytic cascade thio-Michael/ring opening process

cis-β-thio-α-amino acid derivatives through organocatalytic one pot, cascade thio-Michael/ring opening reaction were synthesized in high yields with good diastereoselectivities and enantioselectivities.

Graphical abstract: Enantioselective synthesis of optically active cis-β-thio-α-amino acid derivatives through an organocatalytic cascade thio-Michael/ring opening process
From the themed collection: Organocatalysis
Communication

Diarylprolinol in an asymmetric aldol reaction of an α-alkyl-α-oxo aldehyde as an electrophile

The direct aldol reaction of an α-alkyl-α-oxo aldehyde was catalyzed by trifluoromethyl-substituted diarylprolinol to afford a γ-oxo-β-hydroxy-α-substituted aldehyde in good yield with excellent anti-selectivity and excellent enantioselectivity.

Graphical abstract: Diarylprolinol in an asymmetric aldol reaction of an α-alkyl-α-oxo aldehyde as an electrophile
From the themed collection: Organocatalysis
Communication

Enantioselective organocatalytic reductive amination of aliphatic ketones by benzothiazoline as hydrogen donor

The chiral phosphoric acid-catalyzed enantioselective reductive amination of aliphatic ketones with aromatic amines was successfully achieved by the use of benzothiazoline as the hydrogen donor. Corresponding chiral aliphatic amines were obtained in good yield with excellent enantioselectivities under mild reaction conditions.

Graphical abstract: Enantioselective organocatalytic reductive amination of aliphatic ketones by benzothiazoline as hydrogen donor
From the themed collection: Organocatalysis
Communication

Kinetics and mechanism of organocatalytic aza-Michael additions: direct observation of enamine intermediates

Imidazole reacts with the iminium ion 2, and the failure to observe organocatalytic aza-Michael additions of imidazoles to enals is due to unfavourable proton transfer from the imidazolium fragment to the enamine unit in 3c.

Graphical abstract: Kinetics and mechanism of organocatalytic aza-Michael additions: direct observation of enamine intermediates
From the themed collection: Organocatalysis
Communication

Biomimetic catalytic enantioselective decarboxylative aldol reaction of β-ketoacids with trifluoromethyl ketones

A biomimetic organocatalytic enantioselective decarboxylative ketone aldol reaction of β-ketoacids with trifluoromethyl ketones was realized.

Graphical abstract: Biomimetic catalytic enantioselective decarboxylative aldol reaction of β-ketoacids with trifluoromethyl ketones
From the themed collection: Organocatalysis
Communication

Organic base-catalyzed stereodivergent synthesis of (R)- and (S)-3-amino-4,4,4-trifluorobutanoic acids

β-Trifluoromethyl-β-alanine of either (R) or (S) absolute configuration was selectively prepared using base-catalyzed reaction of (S)-N-tert-butanesulfinyl (3,3,3)-trifluoroacetaldimine with dialkyl malonates.

Graphical abstract: Organic base-catalyzed stereodivergent synthesis of (R)- and (S)-3-amino-4,4,4-trifluorobutanoic acids
From the themed collection: Organocatalysis
Communication

Catalytic enantioselective synthesis of β-trifluoromethyl pyrrolines

One-pot enantioselective synthesis of β-trifluoromethylated pyrrolines was developed by the organocatalyzed-conjugated addition of nitromethane to β-trifluoromethylated enones.

Graphical abstract: Catalytic enantioselective synthesis of β-trifluoromethyl pyrrolines
From the themed collection: Organocatalysis
Communication

Phase transfer catalyzed enantioselective cyclopropanation of 4-nitro-5-styrylisoxazoles

Cyclopropanes were prepared in high yields, complete diastereoselection and high enantioselectivity by reacting 4-nitro-5-styrylisoxazoles with 2-bromomalonate esters under phase-transfer catalysis.

Graphical abstract: Phase transfer catalyzed enantioselective cyclopropanation of 4-nitro-5-styrylisoxazoles
From the themed collection: Organocatalysis
Communication

NHC-catalysed diastereoselective synthesis of multifunctionalised piperidines via cascade reaction of enals with azalactones

NHC-catalysed highly diastereoselective synthesis of multifunctionalised piperidines from azalactones is developed.

Graphical abstract: NHC-catalysed diastereoselective synthesis of multifunctionalised piperidines via cascade reaction of enals with azalactones
From the themed collection: Organocatalysis
Communication

Partially saturated fluorinated heterocycles: diastereo- and enantioselective synthesis of β-trifluoromethyl-pyrroline carboxylates

β-Trifluoromethylated pyrroline carboxylates were synthesized by organocatalytic conjugated addition of a glycine imine to β-trifluoromethylated enones, followed by a deprotection/cyclization/dehydration sequence.

Graphical abstract: Partially saturated fluorinated heterocycles: diastereo- and enantioselective synthesis of β-trifluoromethyl-pyrroline carboxylates
From the themed collection: Organocatalysis
Communication

Dioxindole in asymmetric catalytic synthesis: direct access to 3-substituted 3-hydroxy-2-oxindoles via 1,4-additions to nitroalkenes

The asymmetric Michael addition of dioxindoles (3-hydroxy-2-oxindoles, 1) to β-substituted nitroalkenes is presented. The bifunctional primary amine-thiourea catalyst A, by means of a non-covalent-based mode of activation, secures direct and easy access to valuable 3-substituted 3-hydroxyoxindole derivatives with high stereocontrol.

Graphical abstract: Dioxindole in asymmetric catalytic synthesis: direct access to 3-substituted 3-hydroxy-2-oxindoles via 1,4-additions to nitroalkenes
From the themed collection: Organocatalysis
Communication

Poly(methylhydrosiloxane)-supported chiral imidazolinones: new versatile, highly efficient and recyclable organocatalysts for stereoselective Diels–Alder cycloaddition reactions

New, recyclable PMHS-supported chiral imidazolinones promoted the Diels–Alder reaction of dienes with unsaturated aldehydes (up to 93% ee).

Graphical abstract: Poly(methylhydrosiloxane)-supported chiral imidazolinones: new versatile, highly efficient and recyclable organocatalysts for stereoselective Diels–Alder cycloaddition reactions
From the themed collection: Organocatalysis
Communication

Highly efficient asymmetric aldol reaction in brine using a fluorous sulfonamide organocatalyst

A fluorous organocatalyst promotes direct asymmetric aldol reactions of aromatic aldehydes with ketones in brine to afford the corresponding anti-aldol products in high yield with up to 96% ee.

Graphical abstract: Highly efficient asymmetric aldol reaction in brine using a fluorous sulfonamide organocatalyst
From the themed collection: Organocatalysis
Communication

Direct amination of α-substituted nitroacetates using di-tert-butyl azodicarboxylate catalyzed by Hatakeyama's catalyst β-ICD

We report the first example of catalytic asymmetric direct amination of α-monosubstituted nitroacetates using di-tert-butyl azodicarboxylate, catalyzed by Hatakeyama's catalyst β-ICD.

Graphical abstract: Direct amination of α-substituted nitroacetates using di-tert-butyl azodicarboxylate catalyzed by Hatakeyama's catalyst β-ICD
From the themed collection: Organocatalysis
Communication

Enantiomerically enriched trans-diols from alkenes in one pot: a multicatalyst approach

An oligopeptide equipped with catalytic moieties converts simple alkenes into enantiomerically enriched (monoprotected) 1,2-trans-diols and serves as proof-of-principle for multicatalysis.

Graphical abstract: Enantiomerically enriched trans-diols from alkenes in one pot: a multicatalyst approach
From the themed collection: Organocatalysis
Communication

Enantioselective total synthesis of (+)-galbulinvia organocatalytic domino Michael–Michael–aldol condensation

Enantioselective total synthesis of (+)-galbulin via organocatalytic domino Michael–Michael–aldol condensation.

Graphical abstract: Enantioselective total synthesis of (+)-galbulinvia organocatalytic domino Michael–Michael–aldol condensation
From the themed collection: Organocatalysis
Communication

Asymmetric oxidative Lewis base catalysis—unifying iminium and enamine organocatalysis with oxidations

Enantioselective oxidative domino reactions of allylic alcohols to functionalized esters have been developed. The domino oxidation iminium–enamine activation represents a convenient strategy for the enantioselective synthesis of differently substituted aldehydes starting from readily available allylic alcohols.

Graphical abstract: Asymmetric oxidative Lewis base catalysis—unifying iminium and enamine organocatalysis with oxidations
From the themed collection: Organocatalysis
Communication

Discovery of 2-aminobuta-1,3-enynes in asymmetric organocascade catalysis: construction of drug-like spirocyclic cyclohexanes having five to six contiguous stereocenters

We present herein for the first time the asymmetric synthesis of drug-like spiranes having five to six contiguous stereocenters through the reflexive-Michael reaction by using 2-aminobuta-1,3-enyne-catalysis under mild conditions.

Graphical abstract: Discovery of 2-aminobuta-1,3-enynes in asymmetric organocascade catalysis: construction of drug-like spirocyclic cyclohexanes having five to six contiguous stereocenters
From the themed collection: Organocatalysis
Communication

Hexafluorobenzene: a powerful solvent for a noncovalent stereoselective organocatalytic Michael addition reaction

A dramatic enhancement of stereoselectivity has been observed when using C6F6 as an unconventional solvent in the nitro-Michael reaction of 1,3-dicarbonyl compounds catalysed by a commercially available α,α-L-diaryl prolinol. DFT calculations clarified the origin of stereoselectivity and the role of C6F6.

Graphical abstract: Hexafluorobenzene: a powerful solvent for a noncovalent stereoselective organocatalytic Michael addition reaction
From the themed collection: Organocatalysis
Communication

NHC-catalyzed thioesterification of aldehydes by external redox activation

The NHC-catalyzed thioesterification of aldehydes with thiols in the presence of phenazine as a stoichiometric oxidant.

Graphical abstract: NHC-catalyzed thioesterification of aldehydes by external redox activation
From the themed collection: Organocatalysis
Communication

Organocatalytic asymmetric synthesis of 3-difluoroalkyl 3-hydroxyoxindoles

We report the first example of highly enantioselective organocatalytic synthesis of 3-difluoroalkyl substituted 3-hydroxyoxindoles. The total synthesis of the difluoro analogue of convolutamydine E was achieved by this method.

Graphical abstract: Organocatalytic asymmetric synthesis of 3-difluoroalkyl 3-hydroxyoxindoles
From the themed collection: Organocatalysis
Communication

Catalytic [2+2] and [3+2] cycloaddition reactions of allenoates with cyclic ketimines

Catalytic [2+2] and [3+2] annulations of allenoates with cyclic ketimines afforded functionalized sultam-fused azetidines and dihydropyrroles in good yields with high selectivities.

Graphical abstract: Catalytic [2+2] and [3+2] cycloaddition reactions of allenoates with cyclic ketimines
From the themed collection: Organocatalysis
Communication

A catalytic version of hypervalent aryl-λ3-iodane-induced Hofmann rearrangement of primary carboxamides: iodobenzene as an organocatalyst and m-chloroperbenzoic acid as a terminal oxidant

The first catalytic aryl-λ3-iodane-induced Hofmann rearrangement of primary carboxamides using iodobenzene (5 mol%) and m-CPBA was developed.

Graphical abstract: A catalytic version of hypervalent aryl-λ3-iodane-induced Hofmann rearrangement of primary carboxamides: iodobenzene as an organocatalyst and m-chloroperbenzoic acid as a terminal oxidant
From the themed collection: Organocatalysis
Communication

Organocatalytic asymmetric tandem condensation–intramolecular rearrangement–protonation: an approach to optically active α-amino thioester derivatives

A conceptually novel chiral Brønsted base/Brønsted acid catalytic method for the enantioselective synthesis of α-amino thioesters through a tandem condensation–intramolecular rearrangement–protonation has been developed which provides a number of important synthetic building blocks in good yield and with moderate to good enantioselectivities.

Graphical abstract: Organocatalytic asymmetric tandem condensation–intramolecular rearrangement–protonation: an approach to optically active α-amino thioester derivatives
From the themed collection: Organocatalysis
Open Access Communication

Design, synthesis, and application of tartaric acid derived N-spiro quaternary ammonium salts as chiral phase-transfer catalysts

A novel class of tartaric acid-derived N-spiro quaternary ammonium salts was synthesised starting from known TADDOLs. These compounds were found to catalyse the asymmetric α-alkylation of glycine Schiff bases with high enantioselectivities and in good yields.

Graphical abstract: Design, synthesis, and application of tartaric acid derived N-spiro quaternary ammonium salts as chiral phase-transfer catalysts
From the themed collection: Organocatalysis
Communication

Highly enantioselective Friedel–Crafts alkylation reaction catalyzed by rosin-derived tertiary aminethiourea: synthesis of modified chromanes with anticancer potency

Synthesis and preliminary biological evaluation of various modified chromanes via a highly enantioselective Friedel–Crafts alkylation reaction is disclosed for the first time.

Graphical abstract: Highly enantioselective Friedel–Crafts alkylation reaction catalyzed by rosin-derived tertiary amine–thiourea: synthesis of modified chromanes with anticancer potency
From the themed collection: Organocatalysis
Communication

Highly diastereoselective and enantioselective Michael addition of 5H-oxazol-4-ones to α,β-unsaturated ketones catalyzed by a new bifunctional organocatalyst with broad substrate scope and applicability

A new thiourea–tertiary amine bifunctional catalyst from L-tert-leucine provides excellent stereocontrol in a Michael addition of 5H-oxazol-4-ones to α,β-unsaturated ketones with broad substrate scope and applicability.

Graphical abstract: Highly diastereoselective and enantioselective Michael addition of 5H-oxazol-4-ones to α,β-unsaturated ketones catalyzed by a new bifunctional organocatalyst with broad substrate scope and applicability
From the themed collection: Organocatalysis
Communication

Synthesis of 3-substituted 1,5-aldehyde estersvia an organocatalytic highly enantioselective conjugate addition of new carbonylmethyl 2-pyridinylsulfone to enals

An efficient organocatalytic enantioselective conjugate addition of new carbonylmethyl 2-pyridinylsulfone to enals has been developed for synthesis of chiral 3-substituted 1,5-aldehyde carbonyls.

Graphical abstract: Synthesis of 3-substituted 1,5-aldehyde estersvia an organocatalytic highly enantioselective conjugate addition of new carbonylmethyl 2-pyridinylsulfone to enals
From the themed collection: Organocatalysis
Communication

Chiral squaramide-catalyzed highly diastereo- and enantioselective direct Michael addition of nitroalkanes to nitroalkenes

An efficient highly diastereo- and enantioselective direct Michael addition of nitroalkanes to nitroalkenes catalyzed by chiral squaramide catalyst with a low catalyst loading (2 mol%) afforded synthetically useful 1,3-dinitro compounds in high yields with high diastereoselectivities (up to 95 : 5 dr) and excellent enantioselectivities (up to 97% ee).

Graphical abstract: Chiral squaramide-catalyzed highly diastereo- and enantioselective direct Michael addition of nitroalkanes to nitroalkenes
From the themed collection: Organocatalysis
Communication

Graphene oxide: an efficient and reusable carbocatalyst for aza-Michael addition of amines to activated alkenes

Graphene oxide is reported as a highly efficient and cost-effective organocatalyst for the aza-Michael addition of amines to activated alkenes.

Graphical abstract: Graphene oxide: an efficient and reusable carbocatalyst for aza-Michael addition of amines to activated alkenes
From the themed collection: Organocatalysis
Communication

Organocatalytic enantioselective (3+2) cycloaddition using stable azomethine ylides

The use of stable isoquinolinium and phthalizinium methylides in the organocatalytic enantioselective (3+2) cycloaddition with enals is presented.

Graphical abstract: Organocatalytic enantioselective (3+2) cycloaddition using stable azomethine ylides
From the themed collection: Organocatalysis
Communication

Transforming terpene-derived aldehydes into 1,2-epoxides via asymmetric α-chlorination: subsequent epoxide opening with carbon nucleophiles

Merging Jørgensen's and MacMillan's organocatalytic aldehyde chlorinations enables the synthesis of chiral vinylcyclopropanes and (−)-cis-aerangis lactone via terpene-derived 1,2-epoxides.

Graphical abstract: Transforming terpene-derived aldehydes into 1,2-epoxides via asymmetric α-chlorination: subsequent epoxide opening with carbon nucleophiles
From the themed collection: Organocatalysis
Communication

Brønsted acid-catalyzed enantioselective Friedländer condensations: achiral amine promoter plays crucial role in the stereocontrol

A highly enantioselective Friedländer condensation has been established by using chiral Brønsted acids in combination with achiral amines to give quinolines in high yields (up to 99%) and with excellent enantioselectivities (up to 95%).

Graphical abstract: Brønsted acid-catalyzed enantioselective Friedländer condensations: achiral amine promoter plays crucial role in the stereocontrol
From the themed collection: Organocatalysis
Communication

New synthesis of spirocycles by utilizing in situ forming hypervalent iodine species

An effective spirocyclization procedure for installing nucleophiles via iodonium(III) salts has been developed using the combination of bis(iodoarene) and mCPBA.

Graphical abstract: New synthesis of spirocycles by utilizing in situ forming hypervalent iodine species
From the themed collection: Organocatalysis
Communication

syn-Selective asymmetric cross-aldol reactions between aldehydes and glyoxylic acid derivatives catalyzed by an axially chiral amino sulfonamide

syn-Selective asymmetric cross-aldol reactions of aldehydes with tert-butyl glyoxylate and glyoxamide 2 were realized by the use of an axially chiral amino sulfonamide (S)-1. The cross-aldol products are readily converted to useful chiral building blocks such as γ-lactone and γ-lactam.

Graphical abstract: syn-Selective asymmetric cross-aldol reactions between aldehydes and glyoxylic acid derivatives catalyzed by an axially chiral amino sulfonamide
From the themed collection: Organocatalysis
Communication

Diastereo- and enantioselective conjugate addition of α-substituted nitroacetates to maleimides under base-free neutral phase-transfer conditions

Highly diastereo- and enantioselective conjugate addition of α-substituted nitroacetates to maleimides under base-free neutral phase-transfer conditions was developed.

Graphical abstract: Diastereo- and enantioselective conjugate addition of α-substituted nitroacetates to maleimides under base-free neutral phase-transfer conditions
From the themed collection: Organocatalysis
Paper

Highly enantioselective synthesis of Warfarin and its analogs catalysed by primary aminephosphinamide bifunctional catalysts

An efficient enantioselective Michael addition of 4-hydroxycoumarin to α,β-unsaturated ketones catalysed by primary amine–phosphinamide bifunctional catalysts afforded Warfarin and its analogs in moderate to excellent yields (up to 99%) and good to excellent enantioselectivities (up to 99% ee).

Graphical abstract: Highly enantioselective synthesis of Warfarin and its analogs catalysed by primary amine–phosphinamide bifunctional catalysts
From the themed collection: Organocatalysis
Paper

Squaramide-catalysed enantio- and diastereoselective sulfa-Michael addition of thioacetic acid to α,β-disubstituted nitroalkenes

A highly enantio- and diastereoselective sulfa-Michael addition of thioacetic acid to α,β-disubstituted nitroalkenes catalysed by a chiral squaramide organocatalyst (0.2 mol%) afforded β-nitro sulfides in excellent yields with good diastereoselectivities and high enantioselectivities (up to 94 : 6 dr, 95% ee). This catalytic reaction can be performed on a 10 gram scale.

Graphical abstract: Squaramide-catalysed enantio- and diastereoselective sulfa-Michael addition of thioacetic acid to α,β-disubstituted nitroalkenes
From the themed collection: Organocatalysis
Paper

Carbonate, acetate and phenolate phosphonium salts as catalysts in transesterification reactions for the synthesis of non-symmetric dialkyl carbonates

Carbonate, acetate and phenolate phosphonium salts are excellent organocatalysts for the transesterification of dimethyl and diethyl carbonate with primary and secondary alcohols, including benzyl alcohol, cyclopentanol, cyclohexanol, and the rather sterically hindered menthol.

Graphical abstract: Carbonate, acetate and phenolate phosphonium salts as catalysts in transesterification reactions for the synthesis of non-symmetric dialkyl carbonates
From the themed collection: Organocatalysis
Paper

Enantioselective synthesis of gabapentin analogues via organocatalytic asymmetric Michael addition of α-branched aldehydes to β-nitroacrylates

Michael addition of α-branched aldehydes to β-nitroacrylates was successfully carried out by using a mixed catalyst consisting of a primary amino acid, L-phenylalanine, and its lithium salt to give β-formyl-β′-nitroesters having a quaternary carbon centre in good yields with high enantioselectivity.

Graphical abstract: Enantioselective synthesis of gabapentin analogues via organocatalytic asymmetric Michael addition of α-branched aldehydes to β-nitroacrylates
From the themed collection: Organocatalysis
Paper

Direct catalytic asymmetric synthesis of highly functionalized (2-ethynylphenyl)alcohols via Barbas–List aldol reaction: scope and synthetic applications

A general approach to high-yielding asymmetric synthesis of (2-ethynylphenyl)alcohols as synthons in medicinal chemistry was achieved through Barbas–List aldol reaction on ketones with 2-alkynylbenzaldehydes in the presence of a catalytic amount of trans-4-OH-L-proline or L-prolinamide derivative.

Graphical abstract: Direct catalytic asymmetric synthesis of highly functionalized (2-ethynylphenyl)alcohols via Barbas–List aldol reaction: scope and synthetic applications
From the themed collection: Organocatalysis
Paper

A tripeptide-like prolinamide-thiourea as an aldol reaction catalyst

A tripeptide-like prolinamide-thiourea catalyst with (S)-proline, (1S,2S)-diphenylethylenediamine and (S)-di-tert-butyl aspartate as building blocks provides the products of the reaction between ketones and aromatic aldehydes in high to quantitative yields and high stereoselectivities (up to 99 : 1 dr and 99% ee).

Graphical abstract: A tripeptide-like prolinamide-thiourea as an aldol reaction catalyst
From the themed collection: Organocatalysis
Paper

Synthesis and evaluation of atropos dihydro-5H-dibenzazepinium halide PTCs derived from α-methylbenzylamine

A short synthetic route to diastereoisomeric atropos dihydro-5H-dibenz[c,e]azepinium salts via reaction of a single enantiomer of (R)-α-methylbenzylamine with a racemic atropos biphenol derivative is described.

Graphical abstract: Synthesis and evaluation of atropos dihydro-5H-dibenzazepinium halide PTCs derived from α-methylbenzylamine
From the themed collection: Organocatalysis
Paper

Polystyrene-supported TBD catalyzed ring-opening of N-tosylaziridines with silylated nucleophiles

Polystyrene-supported TBD (PS-TBD) catalyzes the ring-opening of N-tosylaziridines with silylated nucleophiles to give the corresponding products in high yields. PS-TBD was easily recovered and reused without significant loss of catalytic activity.

Graphical abstract: Polystyrene-supported TBD catalyzed ring-opening of N-tosylaziridines with silylated nucleophiles
From the themed collection: Organocatalysis
84 items - Showing page 1 of 2

About this collection

The peer-reviewed articles in this joint ChemComm-OBC web themed issue highlight recent cutting-edge achievements in the exciting field of organocatalysis.

The guest editors of this issue are Keiji Maruoka (Kyoto University), Hisashi Yamamoto (University of Chicago), Liu-Zhu Gong (University of Science and Technology of China) and Benjamin List (Max-Planck-Institut für Kohlenforschung).

Articles in this web themed issue will be added to the list below as soon as possible, after they are published. Please return to this page frequently to see this collection grow.

For information about submitting to this issue, please see the ChemComm blog.

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