Organocatalyzed Enantioselective Decarboxylative Stereoablation Reaction for the Construction of 3,3′-Disubstituted Oxindoles Using β-Ketoacids and 3-Halooxindoles

被引：84

作者：

Zuo, Jian ^{[1
,2
]}

Liao, Yu-Hua ^{[1
,2
]}

Zhang, Xiao-Mei ^{[1
]}

Yuan, Wei-Cheng ^{[1
]}

机构：

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

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 24期

关键词：

CATALYTIC ASYMMETRIC-SYNTHESIS; MANNICH REACTION; 3-SUBSTITUTED OXINDOLES; MICHAEL ADDITIONS; STEREOSELECTIVE CONSTRUCTION; CONJUGATE ADDITION; HIGHLY EFFICIENT; 3+2 ANNULATION; ALDOL REACTION; KETO ACIDS;

D O I：

10.1021/jo302048v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unprecedented method for the construction of optically active 3,3'-disubstituted oxindoles via an organocatalyzed decarboxylative stereoablation reaction has been developed. We describe the first asymmetric reaction between beta-ketoacids and 3-halooxindoles utilizing an organocatalyst. This method allows for the formation of a variety of 3,3'-disubstituted oxindoles bearing a keto-carbonyl group, which are not easily accessible using other methodologies, in moderate to good yields with high enantioselectivities.

引用

页码：11325 / 11332

页数：8

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