β-amino esters via the Reformatsky reaction:: Restraining effects of the ortho-methoxyphenyl substituent

被引：28

作者：

Adrian, JC ^{[1
]}

Barkin, JL ^{[1
]}

Hassib, L ^{[1
]}

机构：

[1] Union Coll, Dept Chem, Schenectady, NY 12308 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 13期

关键词：

D O I：

10.1016/S0040-4039(99)00248-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

beta-Amino esters are, in most cases, the only products of the Reformatsky reaction in CH2Cl(2) between (methoxycarbonyl)methyl zinc bromide (prepared in-situ) and imines prepared from either an aryl or alkyl aldehyde and o-anisdine (Scheme 2). Restraining properties of the ortho-methoxyphenyl group, which lead to sole formation of the beta-amino ester, are ascribed to the inductive effect of the orthomethoxy substituent. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2457 / 2460

页数：4

共 17 条

[1] STEREOSELECTIVE RING-OPENING OF CHIRAL OXAZOLIDINES BY REFORMATSKY REAGENTS - AN ENANTIOSELECTIVE ENTRY TO BETA-AMINO ESTERS [J].