An exploration of asymmetric Baylis-Hillman reactions catalyzed by quinidine-derived chiral amines

被引：78

作者：

Shi, M ^{[1
]}

Jiang, JK ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 17期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1016/S0957-4166(02)00485-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

We utilized a reported quinidine-derived chiral amine 1 to catalyze the asymmetric Baylis-Hillman reaction of aldehydes with methyl vinyl ketone. The enantioselectivities increase and in some cases, the absolute configuration of the Baylis-Hillman adducts can be inverted by the use of proline or lithium salt additives. The highest ee achieved is 49% with S configuration at the newly formed stereogenic centre. When using chiral amine 1 to catalyze the asymmetric Baylis-Hillman reaction of aldehydes with (alpha)-naphthyl acrylate, ee as high as 92% can be achieved. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1941 / 1947

页数：7

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