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
  • [41] Stereoselective functionalisation of SuperQuat enamides:: asymmetric synthesis of homochiral 1,2-diols and α-benzyloxy carbonyl compounds
    Aciro, Caroline
    Davies, Stephen G.
    Garner, A. Christopher
    Ishii, Yutaka
    Key, Min-Suk
    Ling, Kenneth B.
    Prasad, R. Shyam
    Roberts, Paul M.
    Rodriguez-Solla, Humberto
    O'Leary-Steele, Catherine
    Russell, Angela J.
    Sanganee, Hitesh J.
    Savory, Edward D.
    Smith, Andrew D.
    Thomson, James E.
    TETRAHEDRON, 2008, 64 (39) : 9320 - 9344
  • [42] Ruthenium-Catalyzed Enantioselective Synthesis of β-Amino Alcohols from 1,2-Diols by "Borrowing Hydrogen"
    Putra, Anggi Eka
    Oe, Yohei
    Ohta, Tetsuo
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (27) : 6146 - 6151
  • [43] A novel method of synthesis of 1,2-diketones from 1,2-diols using N-bromosuccinimide
    Khurana, JM
    Kandpal, BM
    TETRAHEDRON LETTERS, 2003, 44 (26) : 4909 - 4912
  • [44] Phosphoramidite Ligands Based on Simple 1,2-Diols: Synthesis, Use in Copper-Catalyzed Asymmetric Additions, and Achirotopic Stereogenic Phosphorus Centres
    Mistry, Nisha
    Fletcher, Stephen P.
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (15) : 2489 - 2496
  • [45] Stereoselective synthesis of optically active α-hydroxy ketones and anti-1,2-diols via asymmetric transfer hydrogenation of unsymmetrically substituted 1,2-diketones
    Koike, T
    Murata, K
    Ikariya, T
    ORGANIC LETTERS, 2000, 2 (24) : 3833 - 3836
  • [46] Ruthenium- and lipase-catalyzed DYKAT of 1,2-diols:: an enantioselective synthesis of syn-1,2-diacetates
    Edin, M
    Martín-Matute, B
    Bäckvall, JE
    TETRAHEDRON-ASYMMETRY, 2006, 17 (04) : 708 - 715
  • [47] The synthesis of cycloalka[b]furans via an Au(I)-catalyzed tandem reaction of 3-yne-1,2-diols
    Liu, Wei-Ting
    Xu, Zheng-Liang
    Mou, Xue-Qing
    Zhang, Bang-Hong
    Bao, Wen
    Wang, Shao-Hua
    Lee, Dongjun
    Lei, Lin-Sheng
    Zhang, Kun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (30) : 6333 - 6337
  • [48] Dichlorotin oxide-catalyzed new direct functionalization of olefins:: synthesis of trans β-azidohydrins and 1,2-diols
    Sakurada, I
    Yamasaki, S
    Kanai, M
    Shibasaki, M
    TETRAHEDRON LETTERS, 2000, 41 (14) : 2415 - 2418
  • [49] An efficient method for selective oxidation of 1,2-diols in water catalyzed by Me2SnCl2
    William, Julius M.
    Kuriyama, Masami
    Onomura, Osamu
    RSC ADVANCES, 2013, 3 (42): : 19247 - 19250
  • [50] Ruthenium(0)-Catalyzed Cycloaddition of 1,2-Diols, Ketols, or Diones via Alcohol-Mediated Hydrogen Transfer
    Sato, Hiroki
    Turnbull, Ben W. H.
    Fukaya, Keisuke
    Krische, Michael J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (12) : 3012 - 3021
12345