A Cation-Directed Enantioselective Sulfur-Mediated Michael/Mannich Three-Component Domino Reaction involving Chalcones as Michael Acceptors

被引：30
作者：
Ding, Ran [1 ]
Zheng, Bo [1 ]
Wang, Yan [1 ]
Peng, Yungui [1 ]
机构：
[1] Southwest Univ, Sch Chem & Chem Engn, Key Lab Appl Chem Chongqing Municipal, Chongqing 400715, Peoples R China
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 17期
基金：
美国国家科学基金会;
关键词：
N-ACYLATED OXAZOLIDIN-2-ONES; DYNAMIC KINETIC RESOLUTION; QUATERNARY AMMONIUM-SALTS; ALKALOID-DERIVED CATALYST; PHASE-TRANSFER CATALYSIS; CONJUGATE ADDITION; ALDOL REACTIONS; ALPHA; BETA-DISUBSTITUTED NITROALKENES; BETA-UNSATURATED ALDEHYDES; BIFUNCTIONAL ORGANOCATALYST;
D O I：
10.1021/acs.orglett.5b01833
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new approach has been developed for an asymmetric sulfur-mediated three-component intermolecular Michael/Mannich domino reaction using chalcones as Michael acceptors. This reaction is catalyzed by chiral quaternary ammonium salts derived from modified quinine and provides facile access to complex sulfur-containing compounds with three contiguous stereogenic centers in yields of up to 93%, with 95:5 dr and 95% ee. These compounds were further elaborated to give the equivalent of a chiral aza-Morita-Baylis-Hillman reaction involving chalcones and azetidines bearing four chiral centers.
引用
收藏
页码：4128 / 4131
页数：4
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