A cinchona alkaloid catalyzed enantioselective sulfa-Michael/aldol cascade reaction of isoindigos: construction of chiral bispirooxindole tetrahydrothiophenes with vicinal quaternary spirocenters

被引：59
作者：
Gui, Yong-Yuan [1 ,2 ]
Yang, Jian [1 ,2 ]
Qi, Liang-Wen [1 ,2 ]
Wang, Xiao [1 ,2 ]
Tian, Fang [1 ]
Li, Xiao-Nian [3 ]
Peng, Lin [1 ]
Wang, Li-Xin [1 ]
机构：
[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu 610041, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100039, Peoples R China
[3] Chinese Acad Sci, State Key Lab Phytochem & Plant Resources West Ch, Kunming Inst Bot, Kunming 650201, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 22期
基金：
中国国家自然科学基金;
关键词：
SPIROCYCLOPENTANE BIOXINDOLES; ISOTHIOCYANATO OXINDOLES; SPIROCYCLIC OXINDOLES; ASYMMETRIC-SYNTHESIS; 3+2 CYCLOADDITION; HIGHLY EFFICIENT; STEREOCENTERS; DERIVATIVES; STRATEGY; SPIROOXINDOLES;
D O I：
10.1039/c5ob00774g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A cinchona alkaloid catalyzed diastereoselective and enantioselective sulfa-Michael/aldol cascade reaction between 1,4-dithiane-2,5-diol and isoindigos has been successfully developed to afford the highly congested bispirooxindole tetrahydrothiophenes with vicinal quaternary spirocenters in high yields (up to 91%), excellent diastereoselectivities (up to >20 : 1 dr), and good enantioselectivities (up to 98% ee). Some synthetic transformations of the reaction products were also studied.
引用
收藏
页码：6371 / 6379
页数：9
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