Highly Efficient Synthesis of Heterocyclic and Alicyclic 2-Amino Acid Derivatives by Catalytic Asymmetric Hydrogenation

被引：8

作者：

Li, Lanning ^{[1
]}

Chen, Bin ^{[1
]}

Ke, Yuanyuan ^{[1
]}

Li, Qing ^{[1
]}

Zhuang, Yue ^{[1
]}

Duan, Kun ^{[1
]}

Huang, Yichun ^{[1
]}

Pang, Jiyan ^{[1
]}

Qiu, Liqin ^{[1
,2
]}

机构：

[1] Sun Yat Sen Univ, Sch Chem & Chem Engn, Guangdong Engn Res Ctr Chiral Drugs, Guangzhou 510275, Guangdong, Peoples R China

[2] Sun Yat Sen Univ, Huizhou Res Inst, Dayawan, Huizhou, Peoples R China

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2013年 / 8卷 / 09期

基金：

中国国家自然科学基金;

关键词：

amino acids; asymmetric catalysis; heterocycles; hydrogenation; rhodium; BETA-AMINO ACIDS; BAYLIS-HILLMAN REACTION; ENANTIOSELECTIVE CONJUGATE ADDITION; BETA(2)-AMINO ACIDS; STEREOSELECTIVE-SYNTHESIS; ALPHA-AMINOMETHYLACRYLATES; MICHAEL ADDITION; NITRO ACRYLATES; NITROACRYLATES; METHODOLOGY;

D O I：

10.1002/asia.201300339

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A valuable class of new heterocyclic and alicyclic prochiral -aminomethylacrylates has been conveniently synthesized through a three-step transformation involving a Baylis-Hillman reaction, O-acetylation, and a subsequent allylic amination. The corresponding novel 2-amino acid derivatives were prepared with excellent enantioselectivities and high yields by catalytic asymmetric hydrogenation using the catalyst rhodium(Et-Duphos) (Et-Duphos=2,5,2,5-tetraethyl-1,2-bis(phospholanyl)benzene)) under mild reaction conditions (up to 99% ee and S/C=1000). The influence of the substrate on the enantioselectivity and reactivity is investigated, and the most suitable substrate configuration for the highly efficient enantioselective hydrogenation of -substituted -aminomethylacrylates under the Rh-Duphos system is reported. The current protocol provides a very practical, facile, and scalable method for the preparation of heterocyclic and alicyclic 2-amino acids and their derivatives.

引用

页码：2167 / 2174

页数：8

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