Development of a general, enantioselective organocatalytic Mukaiyama-Michael reaction with α,β-unsaturated aldehydes

TETRAHEDRON

卷:65

Article; Proceedings Paper

Borths, Christopher J.^1,2  Carrera, Diane E.^1,2  MacMillan, David W. C.^1,2 

[1] Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA

[2] CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA

关键词: Mukaiyama-Michael;    Enantioselective organocatalysis;   

DOI  :  10.1016/j.tet.2009.06.066

来源: Elsevier

【 摘 要 】

LUMO-lowering organocatalysis has been extended to promote the conjugate addition of S-alkyl and 1-pyrrolyl silylketene acetals to alpha,beta-unsaturated aldehydes, yielding both, syn and anti Mukaiyama-Michael products with high levels of enantioselectivity. This strategy allows for the generation of chemically useful 1,5-dicarbonyl systems and again highlights the utility of organocatalysis. (C) 2009 Published by Elsevier Ltd.

【 授权许可】

Free