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

被引：26
|
作者：
Borths, Christopher J. [1 ,2 ]
Carrera, Diane E. [1 ,2 ]
MacMillan, David W. C. [1 ,2 ]
机构：
[1] Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
[2] CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA
来源：
TETRAHEDRON | 2009年 / 65卷 / 33期
关键词：
Mukaiyama-Michael; Enantioselective organocatalysis; BIS(OXAZOLINE) COPPER(II) COMPLEXES; CATALYZED ASYMMETRIC 1,4-ADDITION; CHIRAL LEWIS-ACIDS; SILYL ENOL ETHERS; SILYLKETENE ACETALS; ADDITIONS; DERIVATIVES; KETONES;
D O I：
10.1016/j.tet.2009.06.066
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
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.
引用
收藏
页码：6746 / 6753
页数：8
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