Organocatalytic Enantioselective Stereoablative Hydroxylation of 3-Halooxindoles: An Effective Method for the Construction of Enantioenriched 3-Substituted 3-Hydroxy-2-Oxindoles

被引：46

作者：

Liao, Yu-Hua ^{[1
,3
]}

Wu, Zhi-Jun ^{[2
]}

Han, Wen-Yong ^{[1
,3
]}

Zhang, Xiao-Mei ^{[1
]}

Yuan, Wei-Cheng ^{[1
]}

机构：

[1] Chinese Acad Sci, Natl Engn Res Ctr Chiral Drugs, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China

[2] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China

[3] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2012年 / 18卷 / 29期

关键词：

alkaloids; asymmetric catalysis; organocatalysis; oximes; oxindoles; ASYMMETRIC ALDOL REACTION; CONJUGATE ADDITION; STEREOSELECTIVE-SYNTHESIS; OXINDOLES BEARING; MICHAEL ADDITIONS; ISATINS; KETONES; FACILE; 3-HYDROXYOXINDOLES; SPIROOXINDOLES;

D O I：

10.1002/chem.201201395

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

3-Substituted oxindoles as electrophilic partners: An unprecedented method for the construction of hydroxylated 3-substituted oxindoles in high yields and excellent enantioselectivities through stereoablative hydroxylation of 3-halooxindoles with an organocatalyst has been developed. This process not only differs from the common convention of using 3-substituted oxindoles as nucleophiles, but also provides a viable entry to optically active 3-substituted 3-hydroxy-2-oxindoles (see scheme). © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：8916 / 8920

页数：5

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