Models for stereoselective additions to chiral allylic ethers: Osmium tetroxide bis-hydroxylations

被引：67

作者：

Haller, J ^{[1
]}

Strassner, T ^{[1
]}

Houk, KN ^{[1
]}

机构：

[1] UNIV CALIF LOS ANGELES,DEPT CHEM & BIOCHEM,LOS ANGELES,CA 90095

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1997年 / 119卷 / 34期

关键词：

D O I：

10.1021/ja971342g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Density functional calculations (Becke3LYP/6-31G(d)) on the (3 + 2) transition structures of osmium tetroxide mediated dihydroxylations of chiral allylic ethers show that the stereoselectivity is controlled by the ''inside alkoxy effect'' (Stork/Houk-Jager model). In the special case of Z-disubstituted alkenes, 1,3-allylic strain (Kishi model) controls the stereoselectivity.

引用

页码：8031 / 8034

页数：4

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