Catalytic Asymmetric Hydrophosphonylation of Ketimines

被引：49
|
作者：
Yin, Liang [1 ]
Bao, Youmei [1 ]
Kumagai, Naoya [1 ]
Shibasaki, Masakatsu [1 ,2 ]
机构：
[1] Inst Microbial Chem BIKAKEN, Shinagawa Ku, Tokyo 1410021, Japan
[2] JST, ACT C, Shinagawa Ku, Tokyo 1410021, Japan
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 28期
关键词：
ALPHA-AMINOPHOSPHONIC ACIDS; ENANTIOSELECTIVE HYDROPHOSPHONYLATION; AMINO PHOSPHONATES; STEREOSELECTIVE-SYNTHESIS; PHOSPHORUS ANALOGS; CONSTRUCTION; IMINES; ALDEHYDES; CONVENIENT; ALDIMINES;
D O I：
10.1021/ja4059316
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Catalytic asymmetric hydrophosphonylation of aromatic and aliphatic N-thiophosphinoyl ketimines with dialkyl phosphite was efficiently promoted by as little as 0.5 mol% of catalyst loading at ambient temperature. The catalyst can be recovered for repeated use, and facile removal of the thiophosphinoyl group allowed for ready access to the phosphonic acid analogue of enantioenriched alpha,alpha-disubstituted alpha-amino acids.
引用
收藏
页码：10338 / 10341
页数：4
相关论文
共 50 条
  • [41] Asymmetric reduction of ketimines with trichlorosilane employing an imidazole derived organocatalyst
    Gautier, Francois-Moana
    Jones, Simon
    Martin, Stephen J.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (02) : 229 - 231
  • [42] Asymmetric Reduction of Aromatic Ketimines in the Presence of Helical Polymer as Catalyst
    Terada, Kayo
    Masuda, Toshio
    Sanda, Fumio
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2009, 47 (19) : 4971 - 4981
  • [43] Asymmetric synthesis of α-aminophosphonates by means of direct organocatalytic three-component hydrophosphonylation
    Wang Lian
    Cui ShuMin
    Meng Wei
    Zhang GuangWu
    Nie Jing
    Ma JunAn
    CHINESE SCIENCE BULLETIN, 2010, 55 (17): : 1729 - 1731
  • [44] A new and highly efficient asymmetric route to cyclic α-amino phosphonates:: The first catalytic enantioselective hydrophosphonylation of cyclic imines catalyzed by chiral heterobimetallic lanthanoid complexes
    Gröger, H
    Saida, Y
    Sasai, H
    Yamaguchi, K
    Martens, J
    Shibasaki, M
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (13) : 3089 - 3103
  • [45] Asymmetric Transfer Hydrogenation of Ketimines by Indoline as Recyclable Hydrogen Donor
    Saito, Kodai
    Miyashita, Hiromitsu
    Akiyama, Takahiko
    ORGANIC LETTERS, 2014, 16 (20) : 5312 - 5315
  • [46] Organocatalytic Asymmetric Hydrophosphonylation/Mannich Reactions Using Thiourea, Cinchona and Bronsted Acid Catalysts
    Bhadury, Pinaki S.
    Li, Hu
    SYNLETT, 2012, (08) : 1108 - 1131
  • [47] DFT Study on Bifunctional Chiral Bronsted Acid-Catalyzed Asymmetric Hydrophosphonylation of Imines
    Yamanaka, Masahiro
    Hirata, Takashi
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (09): : 3266 - 3271
  • [48] Recent Advances in Catalytic Asymmetric C-C Bond-Forming Reactions to Ketimines Promoted by Metal-Based Catalysts
    Kumagai, Naoya
    Shibasaki, Masakatsu
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2015, 88 (04) : 503 - 517
  • [49] Catalytic enantioselective addition of Grignard reagents to aromatic silyl ketimines
    Rong, Jiawei
    Collados, Juan F.
    Ortiz, Pablo
    Jumde, Ravindra P.
    Otten, Edwin
    Harutyunyan, Syuzanna R.
    NATURE COMMUNICATIONS, 2016, 7
  • [50] Catalytic enantioselective addition of Grignard reagents to aromatic silyl ketimines
    Jiawei Rong
    Juan F. Collados
    Pablo Ortiz
    Ravindra P. Jumde
    Edwin Otten
    Syuzanna R. Harutyunyan
    Nature Communications, 7
12345