Themed collection In memory of Stuart Warren
A simple, general and efficient
ketone synthesis via alkylation and dephosphinoylation of β-keto-diphenylphosphine oxides
Ketone alkylations can be achieved selectively via activation with a base-removable diphenylphosphinoyl group.
Thermodynamically controlled cyclisation reactions with double
Enantiomerically enriched C2-symmetric tetrols were synthesised by a route involving a ‘self-metathesis’ reaction with Grubbs' second-generation ruthenium catalyst; these tetrols produced interesting bicyclic products when rearranged under acidic conditions.
Silica gel catalysed generation of episulfonium ions: a mild method for the synthesis of heterocycles
Asymmetric synthesis of trans-disubstituted
cyclopropanes using phosphine oxides and phosphine boranes
A β-phosphinoyl ‘Evans’ enolate does not alkylate, but the corresponding phosphine borane reacts stereoselectively allowing the synthesis of enantiomerically enriched cyclopropanes. DFT calculations show that differences in the additional chelation of phosphine derivatives result in the improvement in reactivity.
Diphenylphosphinoyl-mediated synthesis of ketones
Branched ketones were prepared by successive α- and γ-alkylation followed by basic dephosphinoylation. Mono-alkylation is selective, highly crystalline intermediates are formed and a one-pot strategy is possible.
Asymmetric cyclopropane synthesis via phosphine oxide mediated cascade reactions
A single-step stereospecific cascade cyclopropanation reaction eliminates stereochemical leakage found in an equivalent known two-step procedure.
Synthesis of new water-soluble phosphonium salts and their Wittig reactions in water
Strategies for the stereoselective synthesis of molecules with remote stereogenic centres across a double bond of fixed configuration
An efficient protocol for Sharpless-style racemic dihydroxylation
Asymmetric dihydroxylation of allylic phosphine oxides
Investigation of the configurational stability of lithiated phosphine oxides using diastereomerically pure and enantiomerically enriched phosphine oxides
Asymmetric aldol reactions of achiral 2-phenylsulfanyl aldehydes with small- and medium-sized carbocyclic rings: the synthesis of homochiral spirocyclic lactones, pyrrolidines and tetrahydrofurans
Control over absolute (R,S), relative (syn,anti) and geometrical (E,Z) stereochemistry in the synthesis of allylically substituted alkenes from diphenylphosphinoyl epoxy alcohols
Asymmetric epoxidation and kinetic resolution of allylic phosphine oxides
Additions of lithiated β-hydroxy alkyldiphenylphosphine oxides to aldehydes, and palladium(II)-catalysed allylic transpositions of bis-acetoxy alkyldiphenylphosphine oxides: synthesis of O-protected (E,E)- and (E,Z)hepta-2,4-dien-1-ol and of alkyldiphenylphosphine oxides bearing remotely related chiral centres
Synthesis of cyclic amines and allylic sulfides by phenylthio migration of β-hydroxy sulfides
Stereochemically controlled synthesis of unsaturated alcohols by the Horner–Wittig reaction
Transformation of cyclic α-phenylthio aldehydes by stereoselective aldol reactions and phenylthio migration into spirocyclic lactones and ethers, and E-allylic alcohols with 1,4-related chiral centres
Synthesis of single isomers (E or Z) of unsaturated carboxylic acids by the Horner-Wittig reaction
Applications of the stereochemically-controlled Horner-Wittig reaction: synthesis of feniculin, (E)-non-6-en-1-ol, a pheromone of the mediterranean fruit fly, (E)- and (Z)-dec-5-en-1-ol, tri-substituted alkenes, and (Z)-α-bisabolene
The stereocontrolled Horner-Wittig reaction: synthesis of disubstituted alkenes
Acyl anion equivalents: synthesis of ketones and enones from α-phenylthioalkylphosphine oxides
Regioselectivity and control in alkene formation from a carbonium ion after diphenylphosphinoyl migration
Mechanism of the [1,3] phenylthio shift in the rearrangement of allyl sulphides
Organic synthesis using the mobile activating group, diphenylphosphinoyl
Stuart Warren (24 Dec 1938–22 Mar 2020)
Celebrating the life of Stuart Warren.
About this collection
Professor Stuart Warren, who sadly passed away on 22 March 2020 at the age of 81, was a leader in the field of organic chemistry and a transformative figure in the British academic landscape in the field of chemical synthesis.
In this tribute, his former student and colleague Jonathan Clayden has collated a number of Stuart’s publications across the Royal Society of Chemistry journals, and together with a number of Stuart’s other former students, written a brief Editorial to accompany the collection. The selected publications span his research career and we hope you enjoy revisiting some of his exceptional work.