Enantioselective organocatalytic amine conjugate addition

被引：264

作者：

Chen, Young K. ^{[1
]}

Yoshida, Masanori ^{[1
]}

MacMillan, David W. C. ^{[1
]}

机构：

[1] CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 29期

关键词：

D O I：

10.1021/ja063267s

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first enantioselective organocatalytic amine conjugate addition has been successfully developed. The application of LUMO-lowering iminium catalysis has enabled the highly chemo- and enantioselective 1,4-addition of a rationally designed N-silyloxycarbamate nucleophile (HOMO-raised) to α,β-unsaturated aldehydes. Imidazolidinone 2•pTSA was found to catalyze the addition of various orthogonally N-protected silyloxycarbamate nucleophiles to a range of α,β-unsaturated aldehydes, affording synthetically useful β-amino aldehyde intermediates. The synthetic utility of the protocol was demonstrated in the rapid synthesis of enantioenriched β-amino acids in one operation and 1,3-amino alcohol derivatives in three operations. Copyright © 2006 American Chemical Society.

引用

页码：9328 / 9329

页数：2

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