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
  • [1] NOVEL ELECTRONIC EFFECTS OF REMOTE SUBSTITUENTS ON THE OXAZABOROLIDINE-CATALYZED ENANTIOSELECTIVE REDUCTION OF KETONES
    COREY, EJ
    HELAL, CJ
    TETRAHEDRON LETTERS, 1995, 36 (50) : 9153 - 9156
  • [2] Highly enantioselective synthesis of multifunctionalized allylic building blocks via oxazaborolidine-catalyzed borane reduction
    Cho, BT
    Shin, SH
    TETRAHEDRON, 2005, 61 (29) : 6959 - 6966
  • [3] ALLYLIC ALCOHOLS OF UNEXPECTED CONFIGURATION BY OXAZABOROLIDINE-CATALYZED REDUCTION OF ALPHA,BETA-UNSATURATED KETONES - AN EXPLANATION-BASED ON MO CALCULATIONS
    BACH, J
    BERENGUER, R
    FARRAS, J
    GARCIA, J
    MESEGUER, J
    VILARRASA, J
    TETRAHEDRON-ASYMMETRY, 1995, 6 (11) : 2683 - 2686
  • [4] Noncovalent Interactions in the Oxazaborolidine-Catalyzed Enantioselective Mukaiyama Aldol
    Farrar, Elliot H. E.
    Grayson, Matthew N.
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (15): : 10054 - 10061
  • [5] Enantioselective synthesis of (R)- and (S)-cizolirtine;: Application of oxazaborolidine-catalyzed asymmetric borane reduction to azolyl phenyl ketones
    Torrens, A
    Castrillo, JA
    Claparols, A
    Redondo, J
    SYNLETT, 1999, (06) : 765 - 767
  • [6] ORIGINS OF THE ENANTIOSELECTIVITY OBSERVED IN OXAZABOROLIDINE-CATALYZED REDUCTIONS OF KETONES
    JONES, DK
    LIOTTA, DC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 204 : 21 - ORGN
  • [7] Synthesis of Ro 25-8210 via an enantioselective oxazaborolidine-catalyzed reduction
    Hull, KG
    Visnick, M
    Tautz, W
    Sheffron, A
    TETRAHEDRON, 1997, 53 (37) : 12405 - 12414
  • [8] ORIGINS OF THE ENANTIOSELECTIVITY OBSERVED IN OXAZABOROLIDINE-CATALYZED REDUCTIONS OF KETONES
    JONES, DK
    LIOTTA, DC
    SHINKAI, I
    MATHRE, DJ
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (04): : 799 - 801
  • [9] Influences of electronic effects and anions on the enantioselectivity in the oxazaborolidine-catalyzed asymmetric borane reduction of ketones
    Xu, JX
    Wei, TZ
    Zhang, QH
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (20): : 6860 - 6866
  • [10] Effect of borane source on the enantioselectivity in the enantiopure oxazaborolidine-catalyzed asymmetric borane reduction of ketones
    Wang, Xiao
    Du, Juanjuan
    Liu, Han
    Du, Da-Ming
    Xu, Jiaxi
    HETEROATOM CHEMISTRY, 2007, 18 (07) : 740 - 746
12345