A Strategy Enabling Enantioselective Direct Conjugate Addition of Inert Aryl Methane Nucleophiles to Enals with a Chiral Amine Catalyst under Mild Conditions

被引：66
|
作者：
Li, Tengfei [1 ,2 ]
Zhu, Jin [1 ,2 ]
Wu, Deyan [1 ,2 ]
Li, Xiangmin [1 ,2 ]
Wang, Sinan [1 ,2 ]
Li, Hao [1 ,2 ]
Li, Jian [1 ,2 ]
Wang, Wei [1 ,2 ,3 ]
机构：
[1] E China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab New Drug Design, Shanghai 200237, Peoples R China
[2] E China Univ Sci & Technol, State Key Lab Bioreactor Engn, Shanghai 200237, Peoples R China
[3] Univ New Mexico, Dept Chem & Chem Biol, Albuquerque, NM 87131 USA
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 28期
基金：
美国国家科学基金会; 中国国家自然科学基金;
关键词：
aryl methane; enals; iminium catalysis; Michael addition; organocatalysis; DIPHENYLPROLINOL SILYL ETHER; ORGANOCATALYTIC ASYMMETRIC-SYNTHESIS; 3+3 CYCLOADDITION REACTION; MICHAEL ADDITION; ALPHA; BETA-UNSATURATED ALDEHYDES; 1,3-DICARBONYL COMPOUNDS; NITROALKANES; CYCLIZATION; REAGENT; ACCESS;
D O I：
10.1002/chem.201300304
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Nitro-charged activation: An organocatalytic enantioselective conjugate addition of aryl methyl nucleophiles to enals has been developed to produce ubiquitous chiral benzylic building blocks (see scheme; TES=triethylsilyl). Taking advantage of the strongly electron-withdrawing nature of nitro groups, which can be conveniently transformed into other functionalities, this functionality was incorporated into aromatic systems as a temporary activating group. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：9147 / 9150
页数：4
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