Highly Efficient and Stereocontrolled Construction of 3,3′-Pyrrolidonyl Spirooxindoles via Organocatalytic Domino Michael/Cyclization Reaction

被引：161
作者：
Liu, Xiong-Li [1 ,2 ]
Han, Wen-Yong [1 ,2 ]
Zhang, Xiao-Mei [1 ]
Yuan, Wei-Cheng [1 ]
机构：
[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Natl Engn Res Ctr Chiral Drugs, Chengdu 610041, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 06期
关键词：
ASYMMETRIC ALDOL REACTION; ENANTIOSELECTIVE SYNTHESIS; CONJUGATE ADDITION; STEREOSELECTIVE-SYNTHESIS; ISOTHIOCYANATO OXINDOLES; QUATERNARY STEREOCENTERS; 1,6-MICHAEL ADDITION; ACID-DERIVATIVES; SNAR REACTIONS; CATALYSIS;
D O I：
10.1021/ol400183k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A wide range of structurally diverse 3,3'-thiopyrrolidonyl spirooxindoles bearing three contiguous stereogenic centers can be smoothly obtained via a domino Michael/cyclization reaction between 3-isothiocyanato oxindoles and 3-methyl-4-nitro-5-alkenyl-isoxazoles with commercially available quinine as the catalyst under mild conditions. The protocol is significantly characterized by high reactivity, a low catalyst loading (1 mol %), and an excellent diastereo- and enantioselectivity (up to >99:1 dr and 98% ee).
引用
收藏
页码：1246 / 1249
页数：4
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