(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.
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收藏
页码：611 / 614
页数：4
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