Theoretical rationale for regioselection in phosphine-catalyzed allenoate additions to acrylates, imines, and aldehydes

被引：139

作者：

Dudding, Travis ^{[1
]}

Kwon, Ohyun

Mercier, Evan

机构：

[1] Brock Univ, Dept Chem, St Catharines, ON LS2 3A1, Canada

[2] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 17期

关键词：

D O I：

10.1021/ol061095y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A rationale for regioselection in phosphine-promoted annulations of acrylates, imines, and aldehydes with allenoates has been developed using computation at the B3LYP/6-31G(d) level of theory. The computed transition states revealed that Lewis acid activation, strong hydrogen bonding (H-bonding), and minimization of unfavorable van der Waals contacts are the guiding factors responsible for regioselection. An excellent level of correlation between the calculated regioselectivities and experiment was observed.

引用

页码：3643 / 3646

页数：4

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