Origins of Diastereoselectivity in Lewis Acid Promoted Ketene Alkene [2+2] Cycloadditions

被引：25

作者：

Rasik, Christopher M. ^{[1
]}

Hong, Young J. ^{[2
]}

Tantillo, Dean J. ^{[2
]}

Brown, M. Kevin ^{[1
]}

机构：

[1] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA

[2] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 19期

基金：

美国国家科学基金会;

关键词：

DENSITY; THERMOCHEMISTRY; PATH;

D O I：

10.1021/ol5025184

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A detailed analysis of a Lewis acid promoted ketene-alkene [2 + 2] cycloaddition is reported. The studies have led to a rationalization for an observed inversion of diastereoselectivity between thermally induced and Lewis acid promoted ketene-alkene [2+2] cycloadditions. The model is supported with both experimental and computational results.

引用

页码：5168 / 5171

页数：4

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