TITANIUM-CATALYZED EPOXY HYDROXYLATION OF ALLYLIC ALCOHOLS - A CONVENIENT DIASTEREOSELECTIVE SYNTHESIS OF EPOXY DIOLS

被引:14
作者
ADAM, W
NESTLER, B
机构
[1] Institut für Organische Chemie, Universität Wüirzburg, D-W-8700, Am Hubland
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1993年 / 32卷 / 05期
关键词
D O I
10.1002/anie.199307331
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In a two-step one-pot procedure the allylic alcohol 1 can be converted diastereoselectively into the epoxy diols (S*,R*,S*)- and (S*,R*,R*)-3 (d = 95:5), simply by adding a catalytic amount of Ti(OiPr)4 to a photooxygenated solution of the allylic alcohol 1. and stopping the reaction after the complete conversion of the hydroperoxide (S*,S*)-2. which is present in addition to the R*,S* isomer. TTP = tetraphenylporphyrin. [GRAPHICS]
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页码:733 / 735
页数:3
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