Catalytic Asymmetric Michael Additions of α-Cyanoacetates

被引：91

作者：

Jautze, Sascha ^{[1
]}

Peters, Rene ^{[1
]}

机构：

[1] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany

来源：

SYNTHESIS-STUTTGART | 2010年 / 03期

关键词：

amino acids; asymmetric catalysis; alpha-cyanoacetate; quaternary stereocentre; Michael addition; AZA-CLAISEN REARRANGEMENT; ENANTIOSELECTIVE CONJUGATE ADDITIONS; PINCER PALLADIUM COMPLEXES; CHIRAL DIPHOSPHINE PHTRAP; QUATERNARY STEREOCENTERS; SEMIEMPIRICAL METHODS; ALLYLIC AMINES; ALPHA; BETA-UNSATURATED IMIDES; NONADJACENT STEREOCENTERS; STEREOSELECTIVE-SYNTHESIS;

D O I：

10.1055/s-0029-1218601

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiopure Michael addition products of alpha-cyanoacetates constitute attractive precursors for functionalised quaternary amino acids and other biologically interesting compounds. Since the pioneering work by Ito et al. in 1992 using rhodium(I) in combination with a trans-chelating planar chiral diphosphine, various complementary approaches have been reported; these are critically discussed and compared in this review. The most efficient recent methodologies utilise a bifunctional activation mode; for example, by dinuclear Lewis acid catalysis or by a well-defined hydrogen-bonding network. This strategy can overcome the difficulty that alpha-cyanoacetates are incapable of two-point binding to a Lewis acid thus hampering the differentiation of prochiral enol(ate) faces.

引用

页码：365 / 388

页数：24

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