Unexpected effect of protecting group and solvent on the stereoselectivity of m-CPBA, epoxidation of diprotected cis-4,5-dihydroxycyclohexenes

被引：22

作者：

de Sousa, SE

Kee, A

O'Brien, P ^{[1
]}

Watson, ST

机构：

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

[2] Rhone Poulenc Rorer, Dagenham Res Ctr, Dagenham RM10 7XS, Essex, England

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 02期

关键词：

epoxidation; diastereoselection; protecting groups; solvents and solvent effects;

D O I：

10.1016/S0040-4039(98)02319-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselectivity of m-CPBA epoxidation of diprotected cis-4,5-dihydroxycyclohexenes has been studied as a function of protecting group. solvent and in one example, epoxidising reagent. Three different ways of obtaining high levels of trans diastereoselectivity have been uncovered. In addition, the results suggest that bulky silyl protecting groups (eg triethylsilyl and tert-butyldimethylsilyl) can, in CH2Cl2, behave as moderate cis-directors via hydrogen bonding to m-CPBA. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：387 / 390

页数：4

共 20 条

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