Mechanistic Studies of the CuH-Catalyzed Synthesis of α-Hydroxyallenes

被引：10

作者：

Reeker, Helene ^{[2
]}

Norrby, Per-Ola ^{[1
]}

Krause, Norbert ^{[2
]}

机构：

[1] Univ Gothenburg, Dept Chem & Mol Biol, S-41296 Gothenburg, Sweden

[2] Dortmund Univ Technol, Dept Chem, D-44227 Dortmund, Germany

来源：

ORGANOMETALLICS | 2012年 / 31卷 / 22期

关键词：

COPPER; REDUCTION; ENERGIES;

D O I：

10.1021/om3007129

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The copper hydride catalyzed S(N)2' reduction of propargyl oxiranes is an efficient method for the diastereoselective synthesis of alpha-hydroxyallenes. Herein, we represent a,detailed, computational study of this reaction using density functional theory (DFT), supported by kinetic investigations. The calculations partially validate the previously, proposed reaction mechanism and explain the high anti stereoselectivity of the reaction arising from a diffusion controlled Lewis acid activation of the epoxide-Cu-hydride complex.

引用

页码：8024 / 8030

页数：7

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