A novel and effective chiral phosphoramide catalyst for the borane-mediated asymmetric reduction of prochiral α-halo ketones

被引：28
|
作者：
Basavaiah, D [1 ]
Reddy, GJ [1 ]
Chandrashekar, V [1 ]
机构：
[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India
来源：
TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 04期
关键词：
D O I：
10.1016/S0957-4166(01)00101-X
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The novel chiral phosphoramide, 1,4-bis[(5S)-1,3-diaza-2-phospha-2-oxo-3-phenylbicyclo(3.3.0)octan-2-yl]piperazine, was synthesised and successfully employed as a catalyst in the borane-mediated asymmetric reductions of prochiral cc-halo ketones, providing the corresponding a-halo alcohols in 90-95% enantiomeric purities. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：685 / 689
页数：5
相关论文
共 50 条
  • [41] CATALYTIC ENANTIOSELECTIVE REACTIONS .2. A COMPARISON STUDY OF ASYMMETRIC BORANE REDUCTION OF PROCHIRAL KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES
    CHO, BT
    CHUN, YS
    DAUELSBERG, C
    WALLBAUM, S
    MARTENS, J
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1994, 15 (02) : 101 - 103
  • [42] Asymmetric reduction of aminoketones with borane and chiral oxazaborolidine catalyst
    Zhang, YW
    Shen, ZX
    Qin, HB
    Li, YH
    Yu, KB
    CHINESE JOURNAL OF CHEMISTRY, 2001, 19 (11) : 1130 - 1135
  • [43] Chiral phosphinamides: new catalysts for the asymmetric reduction of ketones by borane
    Burns, B
    King, NP
    Tye, H
    Studley, JR
    Gamble, M
    Wills, M
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (06): : 1027 - 1038
  • [44] Asymmetric reduction of prochiral ketones to chiral alcohols catalyzed by plants tissue
    Yang, Zhong-Hua
    Zeng, Rong
    Yang, Gai
    Wang, Yu
    Li, Li-Zhen
    Lv, Zao-Sheng
    Yao, Man
    Lai, Bin
    JOURNAL OF INDUSTRIAL MICROBIOLOGY & BIOTECHNOLOGY, 2008, 35 (09) : 1047 - 1051
  • [45] Borane-Mediated Asymmetric Reduction of Acetophenone by Enantiopure Aminonaphthols and Aminoalcohols as Catalytic Source
    Cimarelli, Cristina
    Fratoni, Davide
    Palmieri, Gianni
    CHIRALITY, 2010, 22 (07) : 655 - 661
  • [46] Asymmetric borane reduction of prochiral ketones with oxazaborolidines derived from alpha-pinene
    Masui, M
    Shioiri, T
    SYNLETT, 1996, (01) : 49 - &
  • [47] Asymmetric borane reduction of prochiral ketones catalyzed by C3-symmetric sulfonamide
    Li, Gao-Qiang
    Yan, Ze-Yi
    Niu, Yan-Ning
    Wu, Lu-Yong
    Wei, Hai-Long
    Liang, Yong-Min
    TETRAHEDRON-ASYMMETRY, 2008, 19 (07) : 816 - 821
  • [48] ASYMMETRIC BORANE REDUCTION OF ACHIRAL KETONES MEDIATED BY A-CHIRAL OXAZABOROLIDINE DERIVED FROM (-)-EPHEDRINE
    CHO, BT
    CHUN, YS
    TETRAHEDRON-ASYMMETRY, 1992, 3 (12) : 1539 - 1542
  • [49] Asymmetric reduction of prochiral aromatic ketones by borane-amine complexes in the presence of chiral amine-BF3 catalysts
    Periasamy, M.
    Bhaskar Kanth, J. V.
    Kishan Reddy, C.
    Jornal of the Chemical Society. Perkin Transactions 1, (04):
  • [50] (5S)-1,3-Diaza-2-imino-3-phenylbicyclo[3.3.0]octane:: first example of guanidine based in situ recyclable chiral catalytic source for borane-mediated asymmetric reduction of prochiral ketones
    Basavaiah, Deevi
    Rao, Kalapala Venkateswara
    Reddy, Bhavanam Sekhara
    TETRAHEDRON-ASYMMETRY, 2006, 17 (07) : 1036 - 1040
12345