Highly Enantioselective Synthesis of γ-Nitro Heteroaromatic Ketones in a Doubly Stereocontrolled Manner Catalyzed by Bifunctional Thiourea Catalysts Based on Dehydroabietic Amine: A Doubly Stereocontrolled Approach to Pyrrolidine Carboxylic Acids

被引：119
|
作者：
Jiang, Xianxing [1 ]
Zhang, Yifu [1 ]
Chan, Albert S. C. [2 ]
Wang, Rui [1 ,2 ]
机构：
[1] Lanzhou Univ, Inst Biochem & Mol Biol, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
[2] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Kowloon, Hong Kong, Peoples R China
来源：
ORGANIC LETTERS | 2009年 / 11卷 / 01期
基金：
中国国家自然科学基金;
关键词：
ASYMMETRIC MICHAEL ADDITION; CINCHONA ALKALOID DERIVATIVES; DIRECT CONJUGATE ADDITION; ALDOL REACTIONS; MANNICH REACTIONS; ALPHA; BETA-UNSATURATED IMIDES; BETA-NITROSTYRENES; ORGANIC CATALYST; BOND DONORS; NITROOLEFINS;
D O I：
10.1021/ol8025268
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new class of dehydroabietic amine-substituted primary amine-thiourea bifunctional catalysts were designed and synthesized. The doubly stereocontrolled organocatalytic conjugate addition of a variety of heterocycles-bearing ketones to nitroalkenes was Investigated for the first time, affording (S)- or (R)-gamma-nitro heteroaromatic ketones with excellent enantioselectivities (up to ee >99%). Furthermore, the nearly optically pure gamma-nitro heteroaromatic ketones can be readily transformed into chiral pyrrolidine carboxylic acids.
引用
收藏
页码：153 / 156
页数：4
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