Themed collection Site-selective molecular transformations

21 items
Open Access Feature Article

Enzymatic site-selectivity enabled by structure-guided directed evolution

This review covers recent advances in the directed evolution of enzymes for controlling site-selectivity of hydroxylation, amination and chlorination.

Graphical abstract: Enzymatic site-selectivity enabled by structure-guided directed evolution
From the themed collection: Site-selective molecular transformations
Communication

Borylated oximes: versatile building blocks for organic synthesis

α-Boryl aldoximes – versatile synthetic intermediates that can be obtained from the corresponding α-boryl aldehydes – give rise to a range of previously inaccessible borylated products.

Graphical abstract: Borylated oximes: versatile building blocks for organic synthesis
From the themed collection: Site-selective molecular transformations
Communication

Catalyst-controlled site-selective asymmetric epoxidation of nerylamine and geranylamine derivatives

Novel catalysts for site- and enantioselective epoxidation of dienyl amine derivatives have been developed.

Graphical abstract: Catalyst-controlled site-selective asymmetric epoxidation of nerylamine and geranylamine derivatives
From the themed collection: Site-selective molecular transformations
Communication

Chiral phosphoric acid-catalyzed desymmetrizative glycosylation of 2-deoxystreptamine and its application to aminoglycoside synthesis

This work describes chiral phosphoric acid (CPA)-catalyzed desymmetrizative glycosylation of meso-diol derived from 2-deoxystreptamine.

Graphical abstract: Chiral phosphoric acid-catalyzed desymmetrizative glycosylation of 2-deoxystreptamine and its application to aminoglycoside synthesis
From the themed collection: Site-selective molecular transformations
Communication

Multinuclear zinc bisamidinate catalyzed asymmetric alkylation of α-ketoesters and its unique chemoselectivity

The multinuclear Zn-bisamidinate catalyst exhibited the preferential alkylation of α-ketoesters even in the presence of aldehydes.

Graphical abstract: Multinuclear zinc bisamidinate catalyzed asymmetric alkylation of α-ketoesters and its unique chemoselectivity
From the themed collection: Site-selective molecular transformations
Communication

Borinic acid-catalyzed stereo- and site-selective synthesis of β-glycosylceramides

Diphenylborinic acid catalysis enables the direct, stereo- and site-selective coupling of glycosyl donors with ceramide lipids. The β-1,1′-linkages accessed through this method are characteristic of mammalian glycosphingolipids that play diverse roles in physiology, human health and disease.

Graphical abstract: Borinic acid-catalyzed stereo- and site-selective synthesis of β-glycosylceramides
From the themed collection: Site-selective molecular transformations
Communication

Cp*CoIII-catalyzed directed C–H trifluoromethylthiolation of 2-phenylpyridines and 6-arylpurines

Cp*CoIII-catalyzed directed C–H trifluoromethylthiolation using N-trifluoromethylthiodibenzenesulfonimide as an electrophilic SCF3 source is described.

Graphical abstract: Cp*CoIII-catalyzed directed C–H trifluoromethylthiolation of 2-phenylpyridines and 6-arylpurines
From the themed collection: Site-selective molecular transformations
Communication

Unique site-selectivity control in asymmetric Michael addition of azlactone to alkenyl dienyl ketones enabled by P-spiro chiral iminophosphorane catalysis

Simultaneous recognition of distance and direction of conjugation from carbonyl in alkenyl dienyl ketones enables a highly site-selective asymmetric 1,6-addition.

Graphical abstract: Unique site-selectivity control in asymmetric Michael addition of azlactone to alkenyl dienyl ketones enabled by P-spiro chiral iminophosphorane catalysis
From the themed collection: Site-selective molecular transformations
Communication

Site-selective carbon–carbon bond formation in unprotected monosaccharides using photoredox catalysis

One-step site-selective, protection group-free synthesis of branched monosaccharides.

Graphical abstract: Site-selective carbon–carbon bond formation in unprotected monosaccharides using photoredox catalysis
From the themed collection: Site-selective molecular transformations
Communication

Phase-transfer catalyzed asymmetric synthesis of α,β-unsaturated γ,γ-disubstituted γ-lactams

The direct, γ-selective vinylogous Michael addition of unsaturated γ-monosubstituted γ-lactams was realized by using chiral phase-transfer catalysis.

Graphical abstract: Phase-transfer catalyzed asymmetric synthesis of α,β-unsaturated γ,γ-disubstituted γ-lactams
From the themed collection: Site-selective molecular transformations
Communication

Site-selective benzoin-type cyclization of unsymmetrical dialdoses catalyzed by N-heterocyclic carbenes for divergent cyclitol synthesis

A highly site-selective NHC-catalyzed benzoin-type cyclization of unsymmetrical dialdoses was achieved.

Graphical abstract: Site-selective benzoin-type cyclization of unsymmetrical dialdoses catalyzed by N-heterocyclic carbenes for divergent cyclitol synthesis
From the themed collection: Site-selective molecular transformations
Communication

Tunable differentiation of tertiary C–H bonds in intramolecular transition metal-catalyzed nitrene transfer reactions

Metal-catalyzed nitrene transfer reactions are an appealing and efficient strategy for accessing tetrasubstituted amines through the direct amination of tertiary C–H bonds.

Graphical abstract: Tunable differentiation of tertiary C–H bonds in intramolecular transition metal-catalyzed nitrene transfer reactions
From the themed collection: Site-selective molecular transformations
Communication

Regioselective SN2 reactions for rapid syntheses of azido-inositols by one-pot sequence-specific nucleophilysis

Sequential nucleophilysis of myo-inositol-disulfonate provides easy access to azido-inositols.

Graphical abstract: Regioselective SN2 reactions for rapid syntheses of azido-inositols by one-pot sequence-specific nucleophilysis
From the themed collection: Site-selective molecular transformations
Communication

Scandium(III) triflate-promoted serine/threonine-selective peptide bond cleavage

The site-selective hydrolysis of peptide bonds at Ser and Thr positions was promoted by scandium(III) triflate with a high conversion yield.

Graphical abstract: Scandium(iii) triflate-promoted serine/threonine-selective peptide bond cleavage
From the themed collection: Site-selective molecular transformations
Communication

Enhanced site-selectivity in acylation reactions with substrate-optimized catalysts on solid supports

A concept for site-selective acylation is presented, using substrate-optimized DMAP–peptide conjugates on a solid support.

Graphical abstract: Enhanced site-selectivity in acylation reactions with substrate-optimized catalysts on solid supports
From the themed collection: Site-selective molecular transformations
Communication

Regio- and stereoselective β-mannosylation using a boronic acid catalyst and its application in the synthesis of a tetrasaccharide repeating unit of lipopolysaccharide derived from E. coli O75

A novel regio- and stereoselective β-mannosylation using 1,2-anhydromannose and a diol sugar acceptor in the presence of a boronic acid catalyst and its application are reported.

Graphical abstract: Regio- and stereoselective β-mannosylation using a boronic acid catalyst and its application in the synthesis of a tetrasaccharide repeating unit of lipopolysaccharide derived from E. coli O75
From the themed collection: Site-selective molecular transformations
Communication

Versatile cross-dehydrogenative coupling of heteroaromatics and hydrogen donors via decatungstate photocatalysis

A facile sunlight-induced derivatization of heteroaromatics via TBADT photocatalyzed C–H functionalization in amides, ethers, alkanes and aldehydes is described.

Graphical abstract: Versatile cross-dehydrogenative coupling of heteroaromatics and hydrogen donors via decatungstate photocatalysis
From the themed collection: Site-selective molecular transformations
Communication

Ascorbate as a pro-oxidant: mild N-terminal modification with vinylboronic acids

The common biocompatible reductant, sodium ascorbate, serves as a “pro-oxidant,” facilitating N-terminal modification with vinylboronic acids in air, with divergent chemoselectivity from copper-catalyzed reactions.

Graphical abstract: Ascorbate as a pro-oxidant: mild N-terminal modification with vinylboronic acids
From the themed collection: Site-selective molecular transformations
Communication

Synthesis of a fluorescent photoaffinity probe of OSW-1 by site-selective acylation of an inactive congener and biological evaluation

A novel fluorescent photoaffinity probe of OSW-1 was prepared in two steps by a sequential site-selective acylation strategy using Me2SnCl2.

Graphical abstract: Synthesis of a fluorescent photoaffinity probe of OSW-1 by site-selective acylation of an inactive congener and biological evaluation
From the themed collection: Site-selective molecular transformations
Communication

Palladium catalyzed selective distal C–H olefination of biaryl systems

In this report, we disclose the distal C–H olefination of biphenyl systems with high regio- and stereo-selectivity and useful synthetic yields.

Graphical abstract: Palladium catalyzed selective distal C–H olefination of biaryl systems
From the themed collection: Site-selective molecular transformations
Communication

Dehydrative condensation of carbonyls with non-acidic methylenes enabled by light: synthesis of benzofurans

Condensation of carbonyls with non-acidic methylenes such as those adjacent to heteroatoms and allylic types to generate C[double bond, length as m-dash]C bonds is challenging but highly desirable.

Graphical abstract: Dehydrative condensation of carbonyls with non-acidic methylenes enabled by light: synthesis of benzofurans
From the themed collection: Site-selective molecular transformations
21 items

About this collection

This web themed collection, guest edited by Takeo Kawabata (Kyoto University) and Mark S. Taylor (University of Toronto) highlights the breadth of ongoing research into the discovery and application of catalytic site-selective molecular transformations illustrating the diverse methods that can be used to achieve site-selectivity in chemical synthesis.

Chemoselectivity and stereoselectivity have been key goals for the development of new synthetic methods. Recently, control of site-selectivity has emerged as an exciting direction for organic chemistry research.

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