One-Pot Tandem Approach to Spirocyclic Oxindoles Featuring Adjacent Spiro-Stereocenters

被引：208
作者：
Liu, Yun-Lin [1 ]
Wang, Xin [2 ]
Zhao, Yu-Lei [1 ]
Zhu, Feng [1 ]
Zeng, Xing-Ping [1 ]
Chen, Long [1 ]
Wang, Cui-Hong [1 ]
Zhao, Xiao-Li [1 ]
Zhou, Jian [1 ]
机构：
[1] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China
[2] Sichuan Univ, Coll Chem, Chengdu 610064, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 51期
关键词：
asymmetric catalysis; heterocycles; organocatalysis; spiro compounds; synthetic methods; ORGANOCATALYTIC ASYMMETRIC-SYNTHESIS; BAYLIS-HILLMAN CARBONATES; 3+2 ANNULATION; ENANTIOSELECTIVE CONSTRUCTION; QUATERNARY STEREOCENTERS; EFFICIENT CONSTRUCTION; CONJUGATE ADDITION; CONCISE SYNTHESIS; ALLYLIC COMPOUNDS; HIGHLY EFFICIENT;
D O I：
10.1002/anie.201307250
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
All in a sequence: An organocatalyzed Morita-Baylis-Hillman (MBH)/bromination/[3+2] annulation sequence for highly stereoselective syntheses of bis(spirooxindole)s featuring adjacent spiro-stereocenters is described. The key step is an unprecedented catalytic asymmetric [3+2] annulation of isatin-derived MBH adducts, containing a tetrasubstituted alkene moiety, with isatins. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：13735 / 13739
页数：5
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