Peptide catalyzed asymmetric conjugate addition reactions of aldehydes to nitroethylene -: A convenient entry into γ2-amino acids

被引：181

作者：

Wiesner, Markus ^{[1
]}

Revell, Jefferson D. ^{[1
]}

Tonazzi, Sandro ^{[1
]}

Wennemers, Helma ^{[1
]}

机构：

[1] Univ Basel, Dept Chem, CH-4056 Basel, Switzerland

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 17期

关键词：

D O I：

10.1021/ja801027s

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The peptide H-D-Pro-Pro-Glu-NH2 is a highly effective catalyst for conjugate addition reactions between aldehydes and nitroethylene. Only 1 mol % of H-D-Pro-Pro-Glu-NH2 and a 1.5-fold excess of aldehyde with respect to nitroethylene suffice to obtain Y-nitroaldehydes and, after reduction, monosubstituted Y-nitroalcohols in excellent yields and optical purities. The products can be readily converted into Y-2-amino acids, thereby opening an effective direct entry into this important class of compounds.

引用

页码：5610 / +

页数：3

共 49 条

[1] Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene [J].