(Z)-3-METHYL-3-PENTEN-2-OL AS STEREOCHEMICAL PROBE FOR 1,2 VERSUS 1,3 ALLYLIC STRAIN IN THE PHOTOOXYGENATION AND EPOXIDATION OF CHIRAL ALLYLIC ALCOHOLS

被引：38

作者：

ADAM, W

NESTLER, B

机构：

[1] Institute of Organic Chemistry, University of Würzburg, D-8700 Würzburg, Am Hubland

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 04期

关键词：

STEREOCHEMICAL PROBE; ALLYLIC STRAIN; SINGLET OXYGEN; ENE REACTION; EPOXIDATION;

D O I：

10.1016/S0040-4039(00)61632-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The importance of 1,2 versus 1,3 allylic strain in hydroxy-directed reactions can be assessed from reactions of (Z)-3-methyl-3-penten-2-ol, which is demonstrated for the ene reaction of singlet oxygen and the epoxidations by m-CPBA and VO(acac)2/t-BuOOH; furthermore these results provide insight into transition state geometries for such hydroxy-directed oxygen transfer reactions.

引用

页码：611 / 614

页数：4

共 13 条

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