A chiral formamide: Design and application to catalytic asymmetric synthesis

被引：100

作者：

Iseki, K ^{[1
]}

Mizuno, S ^{[1
]}

Kuroki, Y ^{[1
]}

Kobayashi, Y ^{[1
]}

机构：

[1] Daikin Ind Ltd, MEC Lab, Ibaraki, Osaka 305, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 18期

关键词：

D O I：

10.1016/S0040-4039(98)00334-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(S,S)-N,N-Bis(-alpha-methylbenzyl)formamide is the first example of chiral formamides that function as Lewis base catalysts to effectively serve catalytic asymmetric synthesis. The chiral formamide in combination with an additive, HMPA, catalyzes allylations of aliphatic aldehydes with allyl- and crotyltrichlorosilanes with high enantioselectivity (up to 98% ee). In the crotylations with (E)-crotyltrichlorosilane, cyclohexanecarboxaldehyde and hydrocinnamaldehyde gave the corresponding anti homoallylic alcohols exclusively with 98 and 94% ee's, respectively. (C) 1998 Elsevier Science Ltd, All rights reserved.

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页码：2767 / 2770

页数：4

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