Rhodium-catalyzed asymmetric 1,4-addition of 2-alkenyl-1,3,2-benzodioxaboroles to α,β-unsaturated ketones

被引：110

作者：

Takaya, Y ^{[1
]}

Ogasawara, M ^{[1
]}

Hayashi, T ^{[1
]}

机构：

[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Kyoto 6068502, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 46期

基金：

日本学术振兴会;

关键词：

D O I：

10.1016/S0040-4039(98)01866-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of 2-alkenyl-1,3,2-benzodioxaboroles, which are readily accessible by hydroboration of alkynes with catecholborane, with alpha,beta-unsaturated ketones in the presence of rhodium/(S)-binap catalyst and triethylamine in dioxane/H2O (10/1) proceeded with high enantioselectivity at 100 degrees C to give high yields of optically active beta-alkenyl ketones of over 90% ee. One pot synthesis of the 1,4-addition product is also successful in the rhodium-catalyzed asymmetric reaction by use of alkenylboranes generated in situ from alkyne and catecholborane. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：8479 / 8482

页数：4

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