SOLVENT EFFECTS IN THE DIMETHYLDIOXIRANE OXIDATION OF ALLYLIC ALCOHOLS - EVIDENCE FOR HYDROGEN-BONDING IN THE DIPOLAR TRANSITION-STATE OF OXYGEN-TRANSFER

被引：48

作者：

ADAM, W ^{[1
]}

SMERZ, AK ^{[1
]}

机构：

[1] UNIV WURZBURG,INST ORGAN CHEM,D-97074 WURZBURG,GERMANY

来源：

TETRAHEDRON | 1995年 / 51卷 / 47期

关键词：

D O I：

10.1016/0040-4020(95)00921-T

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A notably higher diastereoselectivity is observed in the dimemyldioxirane epoxidation of chiral allylic alcohols when less polar solvent mixtures are employed; this is interpreted in terms of a dipolar transition state with OH association through hydrogen bonding to the dioxirane, for which a preferential dihedral angle of >130 degrees is estimated.

引用

收藏

页码：13039 / 13044

页数：6

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