Highly efficient and diastereoselective construction of bispirooxindoles through a cascade Michael-cyclization reaction

被引：14
|
作者：
Wu, Song [1 ]
Zhu, Xingli [1 ]
He, Wujun [1 ]
Wang, Rongming [1 ]
Xie, Xiaohua [1 ]
Qin, Dabin [1 ]
Jing, Linhai [1 ]
Chen, Zeqin [1 ]
机构：
[1] China West Normal Univ, Chem Synth & Pollut Control Key Lab Sichuan Prov, Nanchong 637002, Peoples R China
来源：
TETRAHEDRON | 2013年 / 69卷 / 52期
基金：
中国国家自然科学基金;
关键词：
Bispirooxindole; Isothiocyanato oxindole; Methyleneindolinone; Michael-cyclization reaction; Cascade reaction; ONE-POT SYNTHESIS; CATALYTIC ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; REGIOSELECTIVE SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; 3-ISOTHIOCYANATO OXINDOLES; ISOTHIOCYANATO OXINDOLES; SEQUENTIAL 1,3-DIPOLAR; FACILE SYNTHESIS; SPIROHETEROCYCLIC FRAMEWORK;
D O I：
10.1016/j.tet.2013.11.016
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of bispirooxindole derivatives have been synthesized via a cascade Michael-Cyclization reaction between isothiocyanato oxindoles and methyleneindolinones with high yields (up to 98%) and excellent diastereoselectivities (up to >95:5 dr) under mild conditions. The structure and effect on the reaction of less studied 4-substituted methyleneindolinones have also been investigated. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：11084 / 11091
页数：8
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