Enantioselective rearrangement of a meso-cyclohexene oxide using norephedrine-derived chiral bases

被引：46

作者：

Colman, B

de Sousa, SE

O'Brien, P

Towers, TD

Watson, W

机构：

[1] Lancaster Synth Ltd, Morecambe LA3 3DY, Lancs, England

[2] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 21期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0957-4166(99)00432-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Using a chiral base from a norephedrine-derived diamine, the enantioselective rearrangement of a mesocyclohexene oxide can be performed in 94% yield and with 94% enantioselectivity. The enantioselectivity is lower (86% ee) with the diastereoisomeric chiral base. In order to prepare the diastereoisomeric chiral base, a potentially useful way of converting norephedrine into norpseudophedrine was developed. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：4175 / 4182

页数：8

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