Asymmetric borane reduction of prochiral ketones using imidazolium-tagged sulfonamide catalyst

被引：51
|
作者：
Yang, Shang-Dong
Shi, Yun
Sun, Zhen-Hua
Zhao, Ya-Bin
Liang, Yong-Min [1 ]
机构：
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Solid Lubricat, Lanzhou 730000, Peoples R China
来源：
TETRAHEDRON-ASYMMETRY | 2006年 / 17卷 / 12期
关键词：
D O I：
10.1016/j.tetasy.2006.07.003
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A novel sulfonamide catalyst based on a room temperature ionic liquid (RTIL) has been developed for the enantioselective reduction of ketones in refluxing toluene. The optically active secondary alcohol products were obtained in good enantiomeric excess and excellent yields. The imidazolium-tagged sulfonamide catalyst can be readily recovered and reused four times without any significant loss of catalytic activity. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1895 / 1900
页数：6
相关论文
共 50 条
  • [21] Application of MerCO as a chiral catalyst in asymmetric synthesis: asymmetric borane reduction of ketones
    Yang, TK
    Lee, DS
    TETRAHEDRON-ASYMMETRY, 1999, 10 (03) : 405 - 409
  • [22] Catalytic asymmetric borane reduction of prochiral ketones using chiral camphor-derived mercapto-alcohols
    Zhou, YG
    Hou, XL
    Dai, LX
    CHINESE JOURNAL OF CHEMISTRY, 1998, 16 (03) : 284 - 288
  • [23] 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
  • [24] ASYMMETRIC REDUCTION OF PROCHIRAL AROMATIC KETONES BY BORANE-AMINE COMPLEXES IN THE PRESENCE OF A CHIRAL AMINE-BF3 CATALYST
    KANTH, JVB
    PERIASAMY, M
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (17) : 1145 - 1146
  • [25] Catalytic asymmetric borane reduction of prochiral ketones using chiral camphor-derived mercapto-alcohols
    周永贵
    侯雪龙
    戴立信
    Chinese Journal of Chemistry, 1998, (03) : 284 - 288
  • [26] Synthesis of a new C2-Symmetric chiral catalyst and its application in the catalytic asymmetric borane reduction of prochiral ketones
    Zhou, Yan
    Wang, Wen-Hua
    Dou, Wei
    Tang, Xiao-Llang
    Liu, Wei-Sheng
    CHIRALITY, 2008, 20 (02) : 110 - 114
  • [27] Diphenylamine-derived bis-hydroxyamide catalyzed asymmetric borane reduction of prochiral ketones
    Wang, Jin
    Liu, Han
    Du, Da-Ming
    TETRAHEDRON-ASYMMETRY, 2009, 20 (05) : 605 - 609
  • [28] Studies on the synthesis of squaric acid ephedrine and their application in asymmetric catalytic borane reduction of prochiral ketones
    Lü, SM
    Zhou, HB
    Zhang, J
    Xie, RG
    Zhou, ZY
    Chan, ASC
    Yang, DK
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2001, 22 (11): : 1846 - 1851
  • [29] Synthesis of several polyethers derived from BINOL and their application in the asymmetric borane reduction of prochiral ketones
    Zhang, An-Lin
    Yu, Zeng-da
    Yang, Li-Wen
    Yang, Nian-Fa
    TETRAHEDRON-ASYMMETRY, 2015, 26 (04) : 173 - 179
  • [30] 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
12345