Regio- and diastereoselective catalytic epoxidation of chiral allylic alcohols with hexafluoroacetone perhydrate.: Hydroxy-group directivity through hydrogen bonding

被引：24

作者：

Adam, W ^{[1
]}

Degen, HG ^{[1
]}

Saha-Möller, CR ^{[1
]}

机构：

[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 04期

关键词：

D O I：

10.1021/jo982025a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The threo diastereoselectivity in the catalytic-epoxidation of chiral allylic alcohols with 1,3-allylic strain by hexafluoroacetone perhydrate and its regioselectivity in the epoxidation of 1-methylgeraniol establishes a hydroxy-directing effect through hydrogen bonding between the oxidant and substrate. The higher syn selectivity for the cis than trans isomer of 5-tert-butylcyclohexen-3-ol suggests a hydrogen-bonded transition-state structure similar to that of peracids for this catalytic oxygen-transfer process.

引用

页码：1274 / 1277

页数：4

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