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
  • [31] Asymmetric synthesis of (-)-(2R, 3R, 6S)-Irnigaine
    Ma, N
    Ma, DW
    CHINESE JOURNAL OF CHEMISTRY, 2003, 21 (10) : 1356 - 1359
  • [32] Asymmetric synthesis and receptor pharmacology of the group II mGlu receptor ligand (1S,2R,3R,5R,6S)-2-amino3-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic Acid -: HYDIA
    Woltering, Thomas J.
    Adam, Geo
    Huguenin, Philipp
    Wichmann, Juergen
    Kolczewski, Sabine
    Gatti, Silvia
    Bourson, Anne
    Kew, James N. C.
    Richards, Grayson
    Kemp, John A.
    Mutel, Vincent
    Knoflach, Frederic
    CHEMMEDCHEM, 2008, 3 (02) : 323 - 335
  • [33] The asymmetric synthesis of (2R,3R)- and (2R,3S)-3-methyl-aspartates via an enantiodiscrimination strategy
    Bull, SD
    Davies, SG
    Garner, AC
    Mujtaba, N
    SYNLETT, 2001, (06) : 781 - 784
  • [34] Crystal Structures of Dipeptides Derived from the β-Amino Acids (1R,2S)-2-Aminocyclopentanecarboxylic Acid and (1S,2R,3S)-2-Amino-3-methylcyclopentanecarboxylic Acid
    Abraham, Elin
    Davies, Stephen G.
    Roberts, Paul M.
    Thompson, Amber L.
    Thomson, James E.
    JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 2011, 41 (11) : 1722 - 1728
  • [35] Crystal Structures of Dipeptides Derived from the β-Amino Acids (1R,2S)-2-Aminocyclopentanecarboxylic Acid and (1S,2R,3S)-2-Amino-3-methylcyclopentanecarboxylic Acid
    Elin Abraham
    Stephen G. Davies
    Paul M. Roberts
    Amber L. Thompson
    James E. Thomson
    Journal of Chemical Crystallography, 2011, 41 : 1722 - 1728
  • [36] Practical Isolation of tert-Butyl [(1S,2R)-2-Aminocyclohexyl]carbamate (R)-Mandelate through Diastereomeric Salt Formation under Thermodynamic Control
    Yamamoto, Yuhei
    Yaji, Kentaro
    Ito, Tatsuya
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2022, 26 (10) : 2882 - 2893
  • [37] (2R,3R)-1,4-Dimethoxy-1,1,4,4-tetraphenylbutane-2,3-diol: Valuable reagent in the asymmetric synthesis of organoboronates
    Berg, C. Annette
    Eichenauer, Nils C.
    Pietruszka, Joerg
    PURE AND APPLIED CHEMISTRY, 2012, 84 (11) : 2339 - 2416
  • [38] Design and synthesis of (2R,3S)-iodoreboxetine analogues for SPECT imaging of the noradrenaline transporter
    Jobson, Nicola K.
    Crawford, Andrew R.
    Dewar, Deborah
    Pimlott, Sally L.
    Sutherland, Andrew
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (17) : 4996 - 4998
  • [39] Formal syntheses of (2R,3R)-3-hydroxy pipecolic acid and (2R,3S)-3-hydroxy pipecolic acid from L-ascorbic acid
    Chavan, Subhash P.
    Dumare, Nilesh B.
    Pawar, Kailash P.
    TETRAHEDRON LETTERS, 2015, 56 (06) : 805 - 807
  • [40] Stereoselective synthesis of (2R,5R)- and (2S,5R)-5-hydroxylysine
    van den Nieuwendijk, AMCH
    Kriek, NMAJ
    Brussee, J
    van Boom, JH
    van der Gen, A
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2000, 2000 (22) : 3683 - 3691