An Organocatalytic Cascade Strategy for the Enantioselective Construction of Spirocyclopentane Bioxindoles Containing Three Contiguous Stereocenters and Two Spiro Quaternary Centers

被引:151
作者
Sun, Wangsheng [1 ]
Zhu, Gongming [1 ]
Wu, Chongyang [1 ]
Hong, Liang [1 ]
Wang, Rui [1 ]
机构
[1] Lanzhou Univ, Inst Biochem & Mol Biol, Sch Basic Med Sci, Key Lab Preclin Study New Drugs Gansu Prov,Sch Li, Lanzhou 730000, Peoples R China
关键词
cascade reactions; methyleneindolinone; organocatalysis; spiro compounds; squaramides; CATALYTIC ASYMMETRIC-SYNTHESIS; MICHAEL-ALKYLATION REACTIONS; STRUCTURE-BASED DESIGN; ONE-POT SYNTHESIS; SPIROCYCLIC OXINDOLES; DIELS-ALDER; MULTIPLE STEREOCENTERS; CHIRAL SQUARAMIDES; NATURAL-PRODUCTS; DOMINO REACTIONS;
D O I
10.1002/chem.201200478
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A rapid and efficient organocatalytic cascade sequence for the direct construction of spirocyclopentane bioxindoles has been carried out by using a chiral squaramide catalyst in the presence of a base. This process constitutes a powerful approach to the preparation of biologically important bispirooxindoles in high enantioselectivities (see scheme). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:6737 / 6741
页数:5
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