Highly Efficient and Stereoselective Construction of Dispiro-[oxazolidine-2-thione]bisoxindoles and Dispiro [imidazolidine-2-thione]bisoxindoles

被引：113

作者：

Han, Yan-Yan ^{[1
,3
]}

Chen, Wen-Bing ^{[1
,3
]}

Han, Wen-Yong ^{[1
,3
]}

Wu, Zhi-Jun ^{[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] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China

[3] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 02期

基金：

中国国家自然科学基金;

关键词：

ONE-POT SYNTHESIS; SPIROOXINDOLE DERIVATIVES; AQUEOUS-MEDIUM; STEREOCONTROLLED SYNTHESIS; 3-SUBSTITUTED OXINDOLES; MULTIPLE STEREOCENTERS; SPIROCYCLIC OXINDOLES; MICHAEL ADDITIONS; TERTIARY AMINE; 3+2 ANNULATION;

D O I：

10.1021/ol203081x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and stereoselective reaction between 3-isothiocyanato oxindoles and isatins/isatinimines has been developed to afford structurally diverse dispiro[oxazolidine-2-thione]bisoxindoles and dispiro[imidazolidine-2-thione]bisoxindoles in excellent results under mild conditions. The potential of asymmetric induction by means of a chiral auxiliary was explored. The isomers are separable, and products could be isolated as single diastereomers by column chromatography. Further synthetic transformations of the reaction product were also successfully realized.

引用

页码：490 / 493

页数：4

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