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
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.
引用
收藏
页码:4175 / 4182
页数:8
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