Computational Study of Factors Controlling the Boat and Chair Transition States of Ireland-Claisen Rearrangements

被引：24

作者：

Gul, Seref ^{[2
]}

Schoenebeck, Franziska ^{[1
]}

Aviyente, Viktorya ^{[2
]}

Houk, K. N. ^{[1
]}

机构：

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

[2] Bogazici Univ, Dept Chem, TR-34342 Istanbul, Turkey

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 06期

基金：

美国国家卫生研究院;

关键词：

COPE REARRANGEMENT; STEREOCHEMICAL CONTROL; ACTIVATION-ENERGIES; KINETICS; ENOLATE; 1,5-HEXADIENE; CYCLOHEXANE; INVERSION;

D O I：

10.1021/jo100033d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The origins of the boat transition state preference in the Ireland-Claisen rearrangements Studied experimentally by Kishi and co-workers have been explored computationally with Density Functional Theory. Steric interactions in the chair transition states were identified as the principal reason for the boat transition state preference.

引用

页码：2115 / 2118

页数：4

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