Highly efficient synthesis of spiro[oxazolidine-2-thione-oxindoles] with 3-isothiocyanato oxindoles and aldehydes via an organocatalytic cascade aldol-cyclization reaction

被引：31
|
作者：
Chen, Wen-Bing [1 ,2 ]
Han, Wen-Yong [1 ,2 ]
Han, Yan-Yan [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：
TETRAHEDRON | 2013年 / 69卷 / 26期
关键词：
Asymmetric catalysis; Organocatalysis; Spirooxindoles; Cascade reaction; Thiourea-tertiary amine; CATALYTIC ENANTIOSELECTIVE SYNTHESIS; BIFUNCTIONAL ORGANOCATALYSTS; 3,3'-PYRROLIDONYL SPIROOXINDOLES; STEREOSELECTIVE CONSTRUCTION; MICHAEL/CYCLIZATION REACTION; ISOTHIOCYANATO OXINDOLES; 3-SUBSTITUTED OXINDOLES; MULTIPLE STEREOCENTERS; SPIROCYCLIC OXINDOLES; ASYMMETRIC-SYNTHESIS;
D O I：
10.1016/j.tet.2013.05.002
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly efficient method for the construction of a family of spiro[oxazolidine-2-thione-oxindoles] with 3-isothiocyanato oxindoles and aldehydes via a cascade aldol-cyclization process has been developed. This method provides access to spiro[oxazolidine-2-thione-oxindole] derivatives bearing two vicinal quaternary/tertiary stereocenters in up to 95% yield, 98:2 dr, and 89% ee with a chiral bifunctional thiourea tertiary amine organocatalyst based on DPEN scaffold. Good reactivity was observed and the reaction could be completed within 1.0 min. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5281 / 5286
页数：6
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