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

页码：13735 / 13739

页数：5

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