An Efficient Organocatalytic Method for Highly Enantioselective Michael Addition of Malonates to Enones Catalyzed by Readily Accessible Primary Amine-Thiourea

被引：41

作者：

Dudziniski, Krzysztof ^{[1
]}

Pakulska, Anna M. ^{[1
]}

Kwiatkowski, Piotr ^{[1
]}

机构：

[1] Univ Warsaw, Fac Chem, PL-02093 Warsaw, Poland

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 16期

关键词：

DIRECT CONJUGATE ADDITION; ALPHA; ALPHA-DISUBSTITUTED ALDEHYDES; BETA-UNSATURATED KETONES; ASYMMETRIC-SYNTHESIS; AROMATIC KETONES; DERIVATIVES; (-)-STRYCHNINE; NITROALKANES; ESTERS;

D O I：

10.1021/ol3019055

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical and highly enantioselective Michael addition of malonates to enones catalyzed by simple and readily available bifunctional primary amine-thiourea derived from 1,2-diaminocyclohexane is reported. The addition of weak acids and elevated temperature (ca. 50 degrees C) improved the efficiency of the Michael reaction. This approach enables the efficient synthesis of 1,5-ketoesters with good yields, excellent enantioselectivities (up to 99% ee), and low loading (0.5-5 mol %) of simple chiral primary amine-thiourea catalysts, and is applicable in multigram scale synthesis.

引用

页码：4222 / 4225

页数：4

共 75 条

[1] Organocatalytic asymmetric conjugate additions [J].