Catalytic asymmetric borane reduction of prochiral ketones by the use of diazaborolidine catalysts prepared from chiral β-diamines

被引:34
|
作者
Sato, S [1 ]
Watanabe, H [1 ]
Asami, M [1 ]
机构
[1] Yokohama Natl Univ, Fac Engn, Dept Chem & Biotechnol, Hodogaya Ku, Yokohama, Kanagawa 2408501, Japan
关键词
D O I
10.1016/S0957-4166(00)00414-6
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The catalytic asymmetric borane reduction of prochiral ketones was examined in the presence of chiral diazaborolidine catalysts prepared in situ from chiral P-diamines and borane. Chiral secondary alcohols were obtained with modest to high enantiomeric excesses (up to 92% ee) using (S)-2-[(4-trifluoromethyl)anilinomethyl]indoline 2f. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4329 / 4340
页数:12
相关论文
共 50 条
  • [1] Catalytic asymmetric borane reduction of prochiral ketones by the use of chiral β-diamines
    Asami, M
    Sato, S
    Watanabe, H
    CHEMISTRY LETTERS, 2000, (09) : 990 - 991
  • [2] Towards chiral diamines as chiral catalytic precursors for the borane-mediated enantioselective reduction of prochiral ketones
    Deevi Basavaiah
    Utpal Das
    Suparna Roy
    Journal of Chemical Sciences, 2009, 121 : 1003 - 1010
  • [3] Towards chiral diamines as chiral catalytic precursors for the borane-mediated enantioselective reduction of prochiral ketones
    Basavaiah, Deevi
    Das, Utpal
    Roy, Suparna
    JOURNAL OF CHEMICAL SCIENCES, 2009, 121 (06) : 1003 - 1010
  • [4] Chiral diamides as efficient catalytic precursors for the borane-mediated asymmetric reduction of prochiral ketones
    Basavaiah, Deevi
    Rao, Kalapala Venkateswara
    Reddy, Bhavanam Sekhara
    TETRAHEDRON-ASYMMETRY, 2007, 18 (08) : 968 - 974
  • [5] Asymmetric reduction of prochiral ketones with borane using chiral squaric amino alcohols derived from camphor as catalysts
    Zou, HH
    Hu, J
    Zhang, J
    You, JS
    Ma, D
    Lü, D
    Xie, RG
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2005, 242 (1-2) : 57 - 61
  • [6] Hyperbranched chiral catalysts for the asymmetric reduction of ketones with borane
    Bolm, C
    Derrien, N
    Seger, A
    CHEMICAL COMMUNICATIONS, 1999, (20) : 2087 - 2088
  • [7] Synthesis of several chiral phosphinamides and their application in the asymmetric borane reduction of prochiral ketones
    Li, KY
    Zhou, ZH
    Wang, LX
    Zhou, QL
    Tang, CC
    MAIN GROUP METAL CHEMISTRY, 2002, 25 (11) : 663 - 667
  • [8] Asymmetric borane reduction of prochiral ketones by polymer-supported chiral sulfonamides
    Hu, JB
    Zhao, G
    Yang, GS
    Ding, ZD
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (01): : 303 - 304
  • [9] Synthesis and application of new chiral ligands for the asymmetric borane reduction of prochiral ketones
    Hulst, R
    Heres, H
    Peper, NCMW
    Kellogg, RM
    TETRAHEDRON-ASYMMETRY, 1996, 7 (05) : 1373 - 1384
  • [10] Enantiospecific synthesis of pyridinylmethyl pyrrolidinemethanols and catalytic asymmetric borane reduction of prochiral ketones
    Zhang, YX
    Du, DM
    Chen, X
    Lü, SF
    Hua, WT
    TETRAHEDRON-ASYMMETRY, 2004, 15 (01) : 177 - 182