A practical method for synthesis of terminal 1,2-diols in high enantiomeric excess via oxazaborolidine-catalyzed asymmetric reduction

被引:32
|
作者
Cho, BT [1 ]
Chun, YS [1 ]
机构
[1] Hallym Univ, Dept Chem, Chunchon 200702, Kangwondo, South Korea
关键词
D O I
10.1016/S0957-4166(99)00184-6
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Asymmetric borane reduction of oc-hydroxy ketones protected with a tetrahydropyranyl (THP) group catalyzed by Corey's CBS reagent using N-phenylamine-borane complexes as the hydride source provided the corresponding terminal 1,2-diols with a very high enantiomeric excess. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1843 / 1846
页数:4
相关论文
共 50 条
  • [21] Synthesis of alkenes from 1,2-diols via cyclic sulfates
    Joo, YH
    Jang, DO
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1997, 18 (03) : 263 - 264
  • [22] Quinoline Synthesis by the Reaction of Anilines with 1,2-diols Catalyzed by Iron Compounds
    Khusnutdinov, Ravil
    Bayguzina, Alfiya
    Aminov, Rishat
    Dzhemilev, Usein
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 53 (04) : 1022 - 1029
  • [23] Efficient synthesis of optically active β-hydroxy p-tolylsulfones with very high enantiomeric excess via CBS-oxazaborolidine-catalyzed borane reduction
    Cho, BT
    Kim, DJ
    TETRAHEDRON-ASYMMETRY, 2001, 12 (14) : 2043 - 2047
  • [24] Highly selective hydrolytic kinetic resolution of terminal epoxides catalyzed by chiral (salen)CoIII complexes.: Practical synthesis of enantioenriched terminal epoxides and 1,2-diols
    Schaus, SE
    Brandes, BD
    Larrow, JF
    Tokunaga, M
    Hansen, KB
    Gould, AE
    Furrow, ME
    Jacobsen, EN
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) : 1307 - 1315
  • [25] Asymmetric Diboration of Terminal Alkenes with a Rhodium Catalyst and Subsequent Oxidation: Enantioselective Synthesis of Optically Active 1,2-Diols
    Toribatake, Kenji
    Nishiyama, Hisao
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (42) : 11011 - 11015
  • [26] LIPASE-CATALYZED ENANTIOSELECTIVE TRANSESTERIFICATION OF O-TRITYL 1,2-DIOLS - PRACTICAL SYNTHESIS OF (R)-TRITYLGLYCIDOL
    KIM, MJ
    CHOI, YK
    JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05): : 1605 - 1607
  • [27] A PRACTICAL SYNTHESIS OF 1,2-DIOLS VIA THE INTERMOLECULAR CROSS COUPLING OF ALDEHYDES PROMOTED BY A VANADIUM(II) REAGENT
    FREUDENBERGER, JH
    KONRADI, AJ
    PEDERSEN, SF
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1989, 197 : 158 - ORGN
  • [28] Development of the Enantioselective Addition of Ethyl Diazoacetate to Aldehydes: Asymmetric Synthesis of 1,2-Diols
    Trost, Barry M.
    Malhotra, Sushant
    Koschker, Philipp
    Ellerbrock, Pascal
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (04) : 2075 - 2084
  • [29] Preparation of highly optically pure homochiral sulfide-containing alcohols via oxazaborolidine-catalyzed asymmetric borane reduction of ketones
    Xu, JX
    Wei, TZ
    Xia, JK
    Zhang, Q
    Wu, HS
    CHIRALITY, 2004, 16 (06) : 341 - 346
  • [30] ASYMMETRIC-SYNTHESIS OF SYN 1,2-DIOLS VIA THE REACTION OF ALDEHYDES WITH CHIRAL GAMMA-(TETRAHYDROPYRANYLOXY)ALLYLSTANNANES
    YAMAMOTO, Y
    KOBAYASHI, K
    OKANO, H
    KADOTA, I
    JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (26): : 7003 - 7005