Diastereoselective conjugate addition of Grignard reagents to a homochiral fumaramide derived from Oppolzer's sultam

被引：16

作者：

Reid, GP ^{[1
]}

Brear, KW ^{[1
]}

Robins, DJ ^{[1
]}

机构：

[1] Univ Glasgow, Dept Chem, Glasgow G12 8QQ, Lanark, Scotland

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 05期

关键词：

D O I：

10.1016/j.tetasy.2003.12.010

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Conjugate addition of Grignard reagents to N,N'-fumaroylbis[(2R)-bornane-10,2-sultam] 1 occurred with moderate to high levels of diastereoselectivity. Diastereomeric excesses were estimated by analysis of the H-1 NMR spectra of the succinamide mixtures and enantiomeric excesses from F-19 NMR spectra of the bis Mosher esters of the diols produced by reductive cleavage of the succinamides. Saponification of the succinamides gave the corresponding (R)-succinic acids with ees up to 92% showing that addition of the Grignard reagents takes place selectively on the re-face of 1. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：793 / 801

页数：9

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