Isomerization of Terminal Epoxides by a [Pd-H] Catalyst: A Combined Experimental and Theoretical Mechanistic Study

被引：79

作者：

Vyas, Devendra J. ^{[1
]}

Larionov, Evgeny ^{[1
]}

Besnard, Celine ^{[2
]}

Guenee, Laure ^{[2
]}

Mazet, Clement ^{[1
]}

机构：

[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland

[2] Univ Geneva, Crystallog Lab, CH-1211 Geneva 4, Switzerland

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 16期

关键词：

MEINWALD REARRANGEMENT REACTIONS; SUBSTITUTED BENZYLIC ALDEHYDES; PROMOTED REARRANGEMENT; ASYMMETRIC-SYNTHESIS; ALKYLATION REACTIONS; SELECTIVE SYNTHESIS; OXIDATIVE-ADDITION; KINETIC RESOLUTION; CARBONYL-COMPOUNDS; ALPHA-ALKYLATION;

D O I：

10.1021/ja400325w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An unusual palladium hydride complex has been shown to be a competent catalyst in the isomerization of a variety of terminal and internal epoxides. The reaction displayed broad scope and synthetic utility. Experimental and theoretical evidence are provided for an unprecedented hydride mechanism characterized by two distinct enantio-determining steps. These results hold promise for the development of an enantioselective variant of the reaction.

引用

页码：6177 / 6183

页数：7

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