Enantioselective intramolecular Rauhut-Currier reaction catalyzed by chiral phosphinothiourea

被引:71
|
作者
Gong, Jing-Jing [1 ,2 ]
Li, Tian-Ze [1 ,2 ]
Pan, Kun [1 ,2 ]
Wu, Xin-Yan [1 ,2 ,3 ]
机构
[1] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China
[2] E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China
[3] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
基金
中国国家自然科学基金;
关键词
MORITA-BAYLIS-HILLMAN; AMINO-ACID; PHOSPHINES; CYSTEINE;
D O I
10.1039/c0cc04412a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Chiral organophosphine-catalyzed enantioselective Rauhut-Currier reaction has been disclosed for the first time. With L-valine-derived phosphinothiourea, the intramolecular Rauhut-Currier reaction of bis(enones) was achieved in good yields (up to 99%) with excellent enantioselectivities (up to 99.4% ee).
引用
收藏
页码:1491 / 1493
页数:3
相关论文
共 50 条
  • [1] Highly enantioselective intramolecular Rauhut-Currier reaction catalyzed by chiral thiourea-phosphine
    Zhao, Xuan
    Gong, Jing-Jing
    Yuan, Kui
    Sha, Feng
    Wu, Xin-Yan
    TETRAHEDRON LETTERS, 2015, 56 (19) : 2526 - 2528
  • [2] Enantioselective desymmetrization of cyclohexadienones via an intramolecular Rauhut-Currier reaction of allenoates
    Yao, Weijun
    Dou, Xiaowei
    Wen, Shan
    Wu, Ji'en
    Vittal, Jagadese J.
    Lu, Yixin
    NATURE COMMUNICATIONS, 2016, 7
  • [3] The Intramolecular Allenolate Rauhut-Currier Reaction
    MacKay, James A.
    Landis, Zachary C.
    Motika, Stephen E.
    Kench, Margaret H.
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (17): : 7768 - 7774
  • [4] Development of a Cysteine-Catalyzed Enantioselective Rauhut-Currier Reaction
    Aroyan, Carrie E.
    Dermenci, Alpay
    Miller, Scott J.
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (17): : 5784 - 5796
  • [5] Design, Synthesis, and Application of a Chiral Sulfinamide Phosphine Catalyst for the Enantioselective Intramolecular Rauhut-Currier Reaction
    Su, Xiao
    Zhou, Wei
    Li, Yangyan
    Zhang, Junliang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (23) : 6874 - 6877
  • [6] Cysteine-catalyzed enantioselective Rauhut-Currier reaction: A computational study
    Osuna, Silvia
    Miller, Scott J.
    Houk, K. N.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [7] Highly Enantioselective Intermolecular Rauhut-Currier Reaction of Activated Alkenes Catalyzed by Multifunctional Chiral Phosphine
    Zhou Wei
    Gao Lihua
    Tao Mengna
    Su Xiao
    Zhao Qingjie
    Zhang Juunliang
    ACTA CHIMICA SINICA, 2016, 74 (10) : 800 - 804
  • [8] A Highly Nucleophilic Multifunctional Chiral Phosphane-Catalyzed Asymmetric Intramolecular Rauhut-Currier Reaction
    Zhang, Xiao-Nan
    Shi, Min
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (31) : 6271 - 6279
  • [9] α-Functionalization of 2-Vinylpyridines via a Chiral Phosphine Catalyzed Enantioselective Cross Rauhut-Currier Reaction
    Qin, Cong
    Liu, Yonghai
    Yu, Yang
    Fu, Yiwei
    Li, Hao
    Wang, Wei
    ORGANIC LETTERS, 2018, 20 (05) : 1304 - 1307
  • [10] Enantioselective Synthesis of Chromanones via a Peptidic Phosphane Catalyzed Rauhut-Currier Reaction
    Scanes, Robert J. H.
    Grossmann, Oleg
    Grossmann, Andre
    Spring, David R.
    ORGANIC LETTERS, 2015, 17 (10) : 2462 - 2465