Oxazaborolidine-catalyzed enantioselective reduction of α-methylene ketones to allylic alcohols

被引:14
|
作者
Matsuo, Jun-ichi [1 ]
Kozai, Takaaki [1 ]
Nishikawa, Osamu [1 ]
Hattori, Yu [1 ]
Ishibashi, Hiroyuki [1 ]
机构
[1] Kanazawa Univ, Grad Sch Nat Sci & Technol, Div Pharmaceut Sci, Kanazawa, Ishikawa 9201192, Japan
来源
JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 17期
关键词
D O I
10.1021/jo8011013
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxazaborolidine-catalyzed enantioselective reduction of a-methylene ketones was efficiently carried out by using borane-diethylaniline as a stoichiometric reducing agent. The combination of this method and subsequent hydrogenation of thus-formed allylic alcohol improved stereoselectivity in the reduction of 24-oxocholesteryl ester to 24-(R)-hydroxycholesteryl ester.
引用
收藏
页码:6902 / 6904
页数:3
相关论文
共 50 条
  • [21] ENANTIOSELECTIVE OXAZABOROLIDINE REDUCTION OF KETONES CONTAINING HETEROATOMS
    QUALLICH, GJ
    WOODALL, TM
    TETRAHEDRON LETTERS, 1993, 34 (05) : 785 - 788
  • [22] ENANTIOSELECTIVE OXAZABOROLIDINE REDUCTION OF KETONES CONTAINING HETEROATOMS
    WOODALL, TM
    QUALLICH, GJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 205 : 259 - ORGN
  • [23] Quantum mechanical study of stereoselectivity in the oxazaborolidine-catalyzed reduction of acetophenone
    Alagona, G
    Ghio, C
    Persico, M
    Tomasi, S
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (33) : 10027 - 10039
  • [24] Highly Enantioselective Oxazaborolidine-Catalyzed Reduction of 1,3-Dicarbonyl Compounds: Role of the Additive Diethylaniline
    Chein, Rong-Jie
    Yeung, Ying-Yeung
    Corey, E. J.
    ORGANIC LETTERS, 2009, 11 (07) : 1611 - 1614
  • [25] Effect of temperature on the enantioselectivity in the oxazaborolidine-catalyzed asymmetric reduction of ketones. Noncatalytic borane reduction, a nonneglectable factor in the reduction system
    Xu, JX
    Wei, TZ
    Zhang, QH
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (26): : 10146 - 10151
  • [26] Catalytic enantioselective reactions.: Part 16.: Oxazaborolidine-catalyzed asymmetric borane reduction of α-keto acetals
    Cho, BT
    Chun, YS
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (15): : 2095 - 2100
  • [27] Role of NaBH4 stabilizer in the oxazaborolidine-catalyzed asymmetric reduction of ketones with BH3-THF
    Nettles, SM
    Matos, K
    Burkhardt, ER
    Rouda, DR
    Corella, JA
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (09): : 2970 - 2976
  • [28] ASYMMETRIC BORANE REDUCTION OF KETONES CATALYZED BY OXAZABOROLIDINE
    YOUN, IK
    LEE, SW
    PAK, CS
    TETRAHEDRON LETTERS, 1988, 29 (35) : 4453 - 4456
  • [29] Practical Enantioselective Reduction of Ketones Using Oxazaborolidine Catalysts Generated In Situ from Chiral Lactam Alcohols
    Kawanami, Yasuhiro
    Yanagita, Ryo C.
    MOLECULES, 2018, 23 (10):
  • [30] N-Substituent effects of camphor-derived β-amino alcohols on the stereoselectivity of the oxazaborolidine-catalyzed borane reduction of acetophenone
    Sung, Kuangsen
    Cheng, Gin-Ian
    Chen, Yi-Hui
    ARKIVOC, 2007, : 132 - 136