Enantioselective conjugate addition of 3-fluorooxindoles to vinyl sulfone: an organocatalytic access to chiral 3-fluoro-3-substituted oxindoles

被引：56
作者：
Dou, Xiaowei
Lu, Yixin [1 ]
机构：
[1] Natl Univ Singapore, Inst Life Sci, Dept Chem, Singapore 117543, Singapore
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2013年 / 11卷 / 32期
关键词：
ASYMMETRIC MICHAEL ADDITION; N-FLUOROAMMONIUM SALTS; 3-SUBSTITUTED OXINDOLES; MANNICH REACTION; KETO ESTERS; BMS-204352 MAXIPOST(TM); PHOSPHINES SYNTHESIS; CINCHONA ALKALOIDS; CARBONYL-COMPOUNDS; FACILE ACCESS;
D O I：
10.1039/c3ob41267a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An organocatalytic conjugate addition of prochiral 3-fluorinated oxindoles to vinyl sulfones was described for the first time. In the presence of bifunctional tertiary amine-thiourea catalysts, 3-fluoro-3-substituted oxindole adducts were obtained in excellent yields and with high enantiomeric excesses.
引用
收藏
页码：5217 / 5221
页数：5
相关论文
共 50 条
  • [21] Organocatalytic Asymmetric Michael Addition of 3-Pyrrolyloxindoles to β-Phthalimidonitroethene for the Synthesis of 3,3′-Disubstituted Oxindoles Bearing Contiguous 3,α,β-Triamino Functionality
    You, Yong
    Wu, Zhi-Jun
    Chen, Jian-Feng
    Wang, Zhen-Hua
    Xu, Xiao-Ying
    Zhang, Xiao-Mei
    Yuan, Wei-Cheng
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (13) : 5759 - 5765
  • [22] Highly Enantioselective Fluorination of Unprotected 3-Substituted Oxindoles: One-Step Synthesis of BMS 204352 (MaxiPost)
    Li, Jun
    Cai, Yunfei
    Chen, Weiliang
    Liu, Xiaohua
    Lin, Lili
    Feng, Xiaoming
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (20) : 9148 - 9155
  • [23] Organocatalytic enantioselective aza-Henry reaction of ketimines derived from isatins: access to optically active 3-amino-2-oxindoles
    Kumar, Akshay
    Kaur, Jasneet
    Chimni, Swapandeep Singh
    Jassal, Amanpreet Kaur
    RSC ADVANCES, 2014, 4 (47) : 24816 - 24819
  • [24] An enantioselective conjugate addition reaction of 3-substituted benzothiophen-2-ones and 2-phthalimidoacrylates
    Li, Shoulei
    Zhang, Enge
    Feng, Junjun
    Li, Xin
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (12): : 2301 - 2305
  • [25] Enantioselective synthesis of mixed 3,3′-bisindoles via a phosphine-catalyzed umpolung γ-addition of 3′-indolyl-3-oxindoles to allenoates
    Tasdan, Yildiz
    Mei, Guang-Jian
    Lu, Yixin
    SCIENCE BULLETIN, 2020, 65 (07) : 557 - 563
  • [26] Synthesis of chiral tetronic acid derivatives via organocatalytic conjugate addition of ethyl 4-chloro-3-oxobutanoate to nitroalkenes
    Yan, Yun-yun
    Lu, Rui-jiong
    Wang, Jin-jia
    Xuan, Yi-ning
    Yan, Ming
    TETRAHEDRON, 2012, 68 (31) : 6123 - 6130
  • [27] Organocatalytic Enantioselective Amination of 2-Substituted Indolin-3-ones: A Strategy for the Synthesis of Chiral a-Hydrazino Esters
    Yarlagadda, Suresh
    Ramesh, B.
    Reddy, C. Ravikumar
    Srinivas, L.
    Sridhar, B.
    Reddy, B. V. Subba
    ORGANIC LETTERS, 2017, 19 (01) : 170 - 173
  • [28] Organocatalytic Enantioselective Direct Vinylogous Michael Addition of -Substituted Butenolides to 3-Aroyl Acrylates and 1,2-Diaroylethylenes
    Das, Utpal
    Chen, Yi-Ru
    Tsai, Yi-Ling
    Lin, Wenwei
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (24) : 7713 - 7717
  • [29] Organocatalytic asymmetric conjugate addition of malonates to 3-nitro-2H-chromenes
    Nie, Shao-zhen
    Hu, Zhi-peng
    Xuan, Yi-ning
    Wang, Jin-jia
    Li, Xue-ming
    Yan, Ming
    TETRAHEDRON-ASYMMETRY, 2010, 21 (16) : 2055 - 2059
  • [30] Highly Enantioselective Synthesis of 3-Amino-2-oxindole Derivatives: Catalytic Asymmetric α-Amination of 3-Substituted 2-Oxindoles with a Chiral Scandium Complex
    Yang, Zhigang
    Wang, Zhen
    Bai, Sha
    Shen, Ke
    Chen, Donghui
    Liu, Xiaohua
    Lin, Lili
    Feng, Xiaoming
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (22) : 6632 - 6637
12345