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
来源：
TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 10期
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
  • [1] Facile synthesis of terminal 1,2-diols with high optical purity via oxazaborolidine-catalyzed asymmetric borane reduction
    Cho, BT
    Chun, YS
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (15): : 5280 - 5282
  • [2] A general, practical, and versatile strategy for accessing ω-functional 1,2-diols of high enantiomeric excess
    Hoye, TR
    Mayer, MJ
    Vos, TJ
    Ye, ZX
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23): : 8554 - 8557
  • [3] Convenient synthesis of optically active 1,2-diol monosulfonates and terminal epoxides via oxazaborolidine-catalyzed asymmetric borane reduction of α-sulfonyloxy ketones
    Cho, BT
    Yang, WK
    Choi, OK
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (10): : 1204 - 1211
  • [4] Enantiomeric excess of 1,2-diols by formation of cyclic boronates: an improved method
    Morandi, S
    Caselli, E
    Forni, A
    Bucciarelli, M
    Torre, G
    Prati, F
    TETRAHEDRON-ASYMMETRY, 2005, 16 (17) : 2918 - 2926
  • [5] 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
  • [6] Efficient general synthesis of 1,2- and 1,3-diols in high enantiomeric excess via the intramolecular asymmetric reduction of the corresponding ketoalkyl diisopinocampheylborinate intermediates
    Ramachandran, PV
    Lu, ZH
    Brown, HC
    TETRAHEDRON LETTERS, 1997, 38 (05) : 761 - 764
  • [7] Resolution of Terminal 1,2-Diols via Silyl Transfer
    Sun, Xixi
    Worthy, Amanda D.
    Tan, Kian L.
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (20): : 10494 - 10499
  • [8] Chemoenzymatic synthesis of enantiomerically pure terminal 1,2-diols
    Kamal, A
    Sandbhor, M
    Ahmed, K
    Adil, SF
    Shaik, AA
    TETRAHEDRON-ASYMMETRY, 2003, 14 (24) : 3861 - 3866
  • [9] An efficient synthesis of enantiopure 3-chlorostyrene oxide via oxazaborolidine-catalyzed reduction
    Choi, OK
    Cho, BT
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2000, 32 (05) : 493 - 497
  • [10] Synthesis of β-alkyl cyclopentanones in high enantiomeric excess via copper-catalyzed asymmetric conjugate reduction
    Moritani, Y
    Appella, DH
    Jurkauskas, V
    Buchwald, SL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (28) : 6797 - 6798
12345