Catalytic asymmetric enamine protonation reaction

被引:19
作者
Fu, Niankai [1 ,2 ,3 ]
Zhang, Long [1 ,2 ,3 ]
Luo, Sanzhong [1 ,2 ,3 ]
机构
[1] Chinese Acad Sci, Inst Chem, Key Lab Mol Recognit & Funct, BNLMS, Beijing 100190, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100490, Peoples R China
[3] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300071, Peoples R China
关键词
ENANTIOSELECTIVE BETA-PROTONATION; CONJUGATE ADDITION; VINYL KETONES; COOPERATIVE CATALYSIS; REDUCTIVE AMINATION; MICHAEL ADDITION; ACID; ORGANOCATALYSIS; MECHANISMS; ALKYLATION;
D O I
10.1039/c7ob02615c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantioselective protonation, delivery of a proton to a carbanion intermediate, is the most straightforward and fundamental method for the preparation of a chiral tertiary carbon stereocenter. Recent efforts for this objective have been realized through enamine catalysis, which has now become a prominent catalytic strategy enabling a range of fascinating chiral transformations. This review will summarize recent advances in the field of enantioselective enamine protonation for the synthesis of optically active carbonyl compounds. Dynamic kinetic resolutions of alpha-substituted carbonyl compounds through enamine intermediates will be discussed as well.
引用
收藏
页码:510 / 520
页数:11
相关论文
共 61 条
  • [41] Progress in Catalytic Asymmetric Protonation
    Oudeyer, Sylvain
    Briere, Jean-Franois
    Levacher, Vincent
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (28) : 6103 - 6119
  • [42] Fluoride Anions in Self-Assembled Chiral Cage for the Enantioselective Protonation of Silyl Enol Ethers
    Paladhi, Sushovan
    Liu, Yidong
    Kumar, B. Senthil
    Jung, Min-Jung
    Park, Sang Yeon
    Yan, Hailong
    Song, Choong Eui
    [J]. ORGANIC LETTERS, 2017, 19 (12) : 3279 - 3282
  • [43] Organocatalyzed Dynamic Kinetic Resolution
    Pellissier, Helene
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (05) : 659 - 676
  • [44] Dynamic Kinetic Asymmetric Amination of Alcohols: From A Mixture of Four Isomers to Diastereo- and Enantiopure α-Branched Amines
    Rong, Zi-Qiang
    Zhang, Yao
    Chua, Raymond Hong Bing
    Pan, Hui-Jie
    Zhao, Yu
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (15) : 4944 - 4947
  • [45] Asymmetric Protonation of Cumulenolates: Synthesis of Allenyl Aldehydes Facilitated by an Organomanganese Auxiliary
    Roy, Animesh
    Bhat, Bilal A.
    Lepore, Salvatore D.
    [J]. ORGANIC LETTERS, 2016, 18 (06) : 1230 - 1233
  • [46] Diastereodivergent Asymmetric Sulfa-Michael Additions of α-Branched Enones using a Single Chiral Organic Catalyst
    Tian, Xu
    Cassani, Carlo
    Liu, Yankai
    Moran, Antonio
    Urakawa, Atsushi
    Galzerano, Patrizia
    Arceo, Elena
    Melchiorre, Paolo
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (44) : 17934 - 17941
  • [47] Enantioselective protonation of α-hetero carboxylic acid-derived ketene disilyl acetals under chiral ionic Bronsted acid catalysis
    Uraguchi, Daisuke
    Kizu, Tomohito
    Ohira, Yuki
    Ooi, Takashi
    [J]. CHEMICAL COMMUNICATIONS, 2014, 50 (88) : 13489 - 13491
  • [48] Catalytic Asymmetric Reductive Amination of α-Branched Ketones
    Wakchaure, Vijay N.
    Zhou, Jian
    Hoffmann, Sebastian
    List, Benjamin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (27) : 4612 - 4614
  • [49] Photo-induced Catalytic Asymmetric Free Radical Reactions
    Wang Dehong
    Zhang Long
    Luo Sanzhong
    [J]. ACTA CHIMICA SINICA, 2017, 75 (01) : 22 - 33
  • [50] Enantioselective Nazarov cyclization of indole enones cooperatively catalyzed by Lewis acids and chiral Bronsted acids
    Wang, Guo-Peng
    Chen, Meng-Qing
    Zhu, Shou-Fei
    Zhou, Qi-Lin
    [J]. CHEMICAL SCIENCE, 2017, 8 (10) : 7197 - 7202