Recent Advances on the Organocatalyzed Enantioselective α-heterofunctionalization of Carbonyl Compounds

Gabriela      Guillena; Diego      J. Ramon

doi:10.2174/138527211794072551

Abstract

This review covers literature on organocatalyzed enantioselective α-heterofunctionalization of carbonyl compounds from 2006 to 2009. In this review, we will consider those reactions in which a new carbon-heteroatom bond is formed using a chiral organic molecule as catalyst, excluding those processes, which involve the modification on the hybridization of a previously functionalized carbonyl compound. Using this straightforward synthetic strategy, a wide range of valuable chiral building blocks such as α-amino acids, α-amino alcohols, epoxides, 1,2-diols, α-sulfenylated, α-selenenylated and α-halogenated carbonyl derivatives can be obtained by this simple and advantageous methodology.

Keywords: Enantioselective synthesis, organocatalysis, functionalized carbonyl compounds, amino acids, amino alcohols, halogenated carbonyl compounds, heterofunctionalization, aziridine, O-mesitylenesulfonylhydroxylamine, DMAP, Methoxybenzenesulfonyloxycarbamate, Aziridination, selegiline, pipecolic acid, anisomycin, cermizine, di-tert-butyl azodicarboxylate, imidazolidinone, similar catalysts, 2-acetylcyclopentanone, chiral Brønsted acid, TADDOL, nitrosobenzene, enamine, CHALCOGENATION, Darzens Reaction, chloro-ketoesters, SN2 reaction, chloroacetophenone, Cinchona, (S)-BINOL, CD spectra, glucopyranoside, mannopyranoside, liquid-liquid dichloromethane, (E)-diarylenones, Corey's model, TCCA, TBAB, polyleucine, APTESi, DBU, diarylenone, NsNIPh, cinnamaldehyde, Epibatidine, fosfomycin, diltiazem, oxa-Pictet-Spengler cyclization, atorvastatin, tarchonanthuslactone, (S)-propranolol, (S)-naftopidil, Grignard addition, 2-nitrosotoluene, SET, TEMPO, diarylprolinol, NBoc-oxaziridine, Corey-Fuchs alkynylation, Ohira-Bestmann reagent, Wittig reaction, Selectflour