Asymmetric Mannich-type reactions with a chiral acetate: effect of Lewis acid on activation of aldimine

被引：25

作者：

Saito, S ^{[1
]}

Hatanaka, K ^{[1
]}

Yamamoto, H ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Engn, CREST, Japan Sci & Technol Corp JST, Nagoya, Aichi 4648603, Japan

来源：

TETRAHEDRON | 2001年 / 57卷 / 05期

关键词：

asymmetric reaction; chelation; enolates; imines; Mannich reaction;

D O I：

10.1016/S0040-4020(00)01042-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We introduce here a strategy that enables effective addition of lithium enolates of acetates to aldimines. The new method depends strongly on the use of ortho-alkoxy (or ortho-fluoro) aniline-derived aldimines which found to have a potential effect on the enolate addition. This scope was expanded to the asymmetric process using the chiral acetate, which has optically pure 2,6-bis(2-isopropylphenyl)-3,5-dimethylphenol as a chiral auxiliary with axial chirality. A Lewis acid additive is likely to have a complementary role in the pronounced activation of imine functionalities in the Mannich-type addition of the bulky chiral acetate. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：875 / 887

页数：13

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