A tripeptide-like prolinamide-thiourea as an aldol reaction catalyst

被引：49

作者：

Fotaras, Stamatis ^{[1
]}

Kokotos, Christoforos G. ^{[1
]}

Kokotos, George ^{[1
]}

机构：

[1] Univ Athens, Dept Chem, Organ Chem Lab, Athens 15771, Greece

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 29期

关键词：

PRIMARY AMINE-THIOUREAS; ASYMMETRIC CATALYSIS; L-PROLINETHIOAMIDES; ORGANIC-MOLECULES; ORGANOCATALYSTS; MICHAEL; DERIVATIVES; ENAMINE; ACIDS;

D O I：

10.1039/c2ob25693b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A tripeptide-like prolinamide-thiourea catalyst with (S)-proline, (1S,2S)-diphenylethylenediamine and (S)-di-tert-butyl aspartate as building blocks provides the products of the reaction between ketones and aromatic aldehydes in high to quantitative yields and high stereoselectivities (up to 99 : 1 dr and 99% ee). Both the chiral centers of the diamine unit are essential, while the thiourea hydrogen originating from the amine and the amide hydrogen play a predominant role for the catalyst efficiency.

引用

页码：5613 / 5619

页数：7

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