Design of chiral boronate-substituted acrylanilides. Self-activation and boron-transmitted 1,8-stereoinduction in [4+2] cycloaddition

被引：16

作者：

Kennedy, JWJ ^{[1
]}

Hall, DG ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2003年 / 680卷 / 1-2期

基金：

加拿大自然科学与工程研究理事会;

关键词：

Lewis acids; Diels-Alder reactions; boronate esters; substituent effects; chiral auxiliaries; stereoselective synthesis; remote stereoinduction;

D O I：

10.1016/S0022-328X(03)00400-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The [4 + 2] cycloaddition of ortho-boronoanilide dienophile 4 with cyclopentadiene was found to proceed faster than both its para isomer 8 and the unsubstituted derivative 6, thereby confirming that self-activation by internal coordination is operative in the case of 4. Chiral boronic esters derivatives 9-13 provided a small level of remote 1,8-stereoinduction transmitted through a putative tetrahedral stereogenic boronate complex. These results show that dialkoxyboronic esters can operate as weak, internal Lewis acids and activate carbonyl-containing functionalities in cycloaddition reactions. (C) 2003 Elsevier B.V. All rights reserved.

引用

页码：263 / 270

页数：8

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