Stereospecific conversion of (1R*,3S*)- and (1R*,3R*)-3-cyclohexyl-1-phenylpropane-1,3-diol into the corresponding 2,4-disubstituted oxetanes

被引：14
|
作者：
Aftab, T
Carter, C
Christlieb, M
Hart, J
Nelson, A [1 ]
机构：
[1] Univ Leeds, Sch Chem, Leeds LS2 9JT, W Yorkshire, England
[2] Univ Cambridge, Chem Lab, Cambridge CB2 1EW, England
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 05期
关键词：
D O I：
10.1039/a909163g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Conversion of two diastereoisomeric 1,3-diols (3-cyclohexyl-1-phenylpropane-1,3-diol) into orthoesters was followed by treatment with acetyl bromide. The 1,3-bromo acetates (acetic acid 3-bromo-1-cyclohexyl-3-phenylpropyl esters) were obtained with complete inversion of configuration at a benzylic site. Methanolysis of the bromo acetates, followed by ring-closure, resulted in a second inversion of configuration at a benzylic site to give the corresponding oxetanes with overall retention of configuration.
引用
收藏
页码：711 / 722
页数：12
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