Theoretical study of the mechanism of Hantzsch ester hydrogenation of imines catalyzed by chiral BINOL-phosphoric acids

被引：244

作者：

Simon, Luis ^{[1
]}

Goodman, Jonathan M. ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Unilever Ctr Mol Sci Informat, Cambridge CB2 1EW, England

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 27期

关键词：

D O I：

10.1021/ja800793t

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The mechanism of the Hantzsch ester hydrogenation of imines catalyzed by chiral BINOL-phosphoric acid has been investigated using DFT methods. Despite the importance of this reaction, there are a number of possible detailed mechanisms, and the preferred pathway has not been firmly established. Our calculations show that the catalyst not only activates the imine group for the reaction by acting as a Bronsted acid but also establishes an interaction with the Hantzsch ester that can lead to an explanation for the enantioselectivity.

引用

页码：8741 / 8747

页数：7

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