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
收藏
页码：11325 / 11332
页数：8
相关论文
共 50 条
  • [1] Preparation of 3-Sulfonylated 3,3-Disubstituted Oxindoles by the Addition of Sulfinate Salts to 3-Halooxindoles
    Zuo, Jian
    Wu, Zhi-Jun
    Zhao, Jian-Qiang
    Zhou, Ming-Qiang
    Xu, Xiao-Ying
    Zhang, Xiao-Mei
    Yuan, Wei-Cheng
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (01) : 634 - 640
  • [2] Enantioselective Construction of 3-Hydroxy Oxindoles via Decarboxylative Addition of β-Ketoacids to Isatins
    Zhong, Fangrui
    Yao, Weijun
    Dou, Xiaowei
    Lu, Yixin
    ORGANIC LETTERS, 2012, 14 (15) : 4018 - 4021
  • [3] Organocatalytic Enantioselective Stereoablative Hydroxylation of 3-Halooxindoles: An Effective Method for the Construction of Enantioenriched 3-Substituted 3-Hydroxy-2-Oxindoles
    Liao, Yu-Hua
    Wu, Zhi-Jun
    Han, Wen-Yong
    Zhang, Xiao-Mei
    Yuan, Wei-Cheng
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (29) : 8916 - 8920
  • [4] Enantioselective Synthesis of 3,3-Disubstituted Oxindoles Bearing Two Different Heteroatoms at the C3 Position by Organocatalyzed Sulfenylation and Selenenylation of 3-Pyrrolyl-oxindoles
    You, Yong
    Wu, Zhi-Jun
    Wang, Zhen-Hua
    Xu, Xiao-Ying
    Zhang, Xiao-Mei
    Yuan, Wei-Cheng
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (16) : 8470 - 8477
  • [5] Enantioselective synthesis of 3-hydroxy oxindoles by ytterbium-catalysed decarboxylative addition of β-ketoacids to isatins
    Duan, Zhiqiang
    Han, Jianlin
    Qian, Ping
    Zhang, Zirui
    Wang, Yi
    Pan, Yi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (38) : 6456 - 6459
  • [6] Enantioselective Organocatalytic Addition of Nitroalkanes to Oxindolylideneindolenines for the Construction of Chiral 3,3-Disubstituted Oxindoles
    Huang, Jian-Zhou
    Wu, Xiang
    Gong, Liu-Zhu
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (13) : 2531 - 2537
  • [7] Enantioselective Organocatalyzed Sulfenylation of 3-Substituted Oxindoles
    Li, Xin
    Liu, Cong
    Xue, Xiao-Song
    Cheng, Jin-Pei
    ORGANIC LETTERS, 2012, 14 (17) : 4374 - 4377
  • [8] Organocatalyzed Enantioselective Decarboxylative Mannich Reaction of -Ketoacids with Pyrazolinone Ketimines for the Construction of Chiral -Amino Ketone-Pyrazolinone Derivatives
    Zhou, Yang
    You, Yong
    Wang, Zhen-Hua
    Zhang, Xiao-Mei
    Xu, Xiao-Ying
    Yuan, Wei-Cheng
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (20) : 3112 - 3116
  • [9] Organocatalyzed enantioselective Michael addition/cyclization cascade reaction of 3-isothiocyanato oxindoles with arylidene malonates
    Chowdhury, Raghunath
    Kumar, Mukesh
    Ghosh, Sunil K.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (47) : 11250 - 11260
  • [10] Development of Synthetic Methodologies via Catalytic Enantioselective Synthesis of 3,3-Disubstituted Oxindoles
    Cao, Zhong-Yan
    Zhou, Feng
    Zhou, Jian
    ACCOUNTS OF CHEMICAL RESEARCH, 2018, 51 (06) : 1443 - 1454
12345