Enantioselective synthesis of (1S,2R)-ephenamine

被引:12
|
作者
Kaur, Ramandeep [1 ]
Pandey, Satyendra Kumar [1 ]
机构
[1] Thapar Univ, Sch Chem & Biochem, Patiala 147001, Punjab, India
关键词
ALPHA-AMINO-ACIDS; PRACTICAL CHIRAL AUXILIARY; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; TRANSFER HYDROGENATION; DERIVATIVES; PSEUDOEPHEDRINE; DIHYDROXYLATION; ALKYLATION; ALCOHOLS;
D O I
10.1016/j.tetasy.2016.02.013
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A short and efficient enantioselective synthesis of (15,2R)-ephenamine is described employing Sharpless asymmetric dihydroxylation and regioselective nucleophilic opening of a cyclic sulfite as the key steps. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:338 / 340
页数:3
相关论文
共 50 条
  • [11] Synthesis of (+)-(1S,2R) and (-)-(1R,2S)-2-aminocyclobutane-1-carboxylic acids
    Gauzy, C
    Pereira, E
    Faure, S
    Aitken, DJ
    TETRAHEDRON LETTERS, 2004, 45 (38) : 7095 - 7097
  • [12] (1S,2R)-1-aminoindan-2-ol
    Larrow, JF
    Roberts, E
    Verhoeven, TR
    Ryan, KM
    Senanayake, CH
    Reider, PJ
    Jacobsen, EN
    ORGANIC SYNTHESES, VOL 76 - 1999, 1999, 76 : 46 - 56
  • [13] Imines derived from (1S,2R)-norephedrine as catalysts in the enantioselective addition of diethylzinc to aldehydes
    Jaworska, Magdalena
    Laczkowski, Krzysztof Z.
    Wekniak, Miroslaw
    Welke, Magdalena
    Wojtczak, Andrzej
    APPLIED CATALYSIS A-GENERAL, 2009, 357 (02) : 150 - 158
  • [14] CHEMICAL SYNTHESIS OF THE (1R,2S) AND (1S,2R) ARENE OXIDE METABOLITES OF ACRIDINE
    BOYD, DR
    DORRITY, MRJ
    HAMILTON, L
    MALONE, JF
    SMITH, A
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (19): : 2711 - 2714
  • [15] Enantioselective synthesis of (2R,3S)-(+)-catechin
    Jew, S
    Lim, D
    Bae, S
    Kim, H
    Kim, J
    Lee, J
    Park, H
    TETRAHEDRON-ASYMMETRY, 2002, 13 (07) : 715 - 720
  • [16] Synthesis of (1S,2R,12S)-2-hydroxy-11-dihydroneocembrene
    Kato, T
    Ebihara, S
    Furukawa, T
    Tanahashi, H
    Hoshikawa, M
    TETRAHEDRON-ASYMMETRY, 1999, 10 (19) : 3691 - 3700
  • [17] Quantitative conversion of indene to (1S,2R) indene oxide and (1S,2R)-indandiol by combination of haloperoxidase bioconversion and chemical steps
    Merck & Co Inc, Westfield, NJ, United States
    Biotechnol Adv, 3-4 (800):
  • [18] The Synthesis of (+)-1S,2R,5S-8-β-Naphthylmenthol from R-(+)-Pulegone
    Huang, Guo-Bin
    Wu, Ke-Mei
    Huang, Liang
    Kao Teng Hsueh Hsiao Hua Heush Hsueh Pao/ Chemical Journal of Chinese Universities, 1999, 20 (09):
  • [19] Asymmetric Synthesis of (1S,2R)-(1,2,3-Trihydroxypropyl)diphenylphosphine Oxide
    A. O. Kolodyazhnaya
    V. P. Kukhar'
    O. I. Kolodyazhnyi
    Russian Journal of General Chemistry, 2004, 74 : 965 - 966
  • [20] Asymmetric synthesis of (1S,2R)-(1,2,3-trihydroxypropyl)diphenylphosphine oxide
    Kolodyazhnaya, AO
    Kukhar, VP
    Kolodyazhnyi, OI
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2004, 74 (06) : 965 - 966