Asymmetric synthesis of both the enantiomers of antidepressant venlafaxine and its analogues

被引：12
作者：
Bhuniya, Rajib [1 ]
Nanda, Samik [1 ]
机构：
[1] IIT Kharagpur, Dept Chem, Kharagpur 721302, W Bengal, India
来源：
TETRAHEDRON LETTERS | 2012年 / 53卷 / 15期
关键词：
Antidepressants; Hydroxynitrile lyase; Lipase catalyzed kinetic resolution; Asymmetric synthesis; LYASE-CATALYZED ADDITION; 4-SUBSTITUTED CYCLOHEXANONES; CYANOHYDRINS; DERIVATIVES; ALCOHOLS; HCN;
D O I：
10.1016/j.tetlet.2012.02.025
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Chemoenzymatic asymmetric synthesis of antidepressant agent venlafaxine and its analogue have been reported in this communication. The main highlight of the reported synthesis is the stereoselective synthesis of cyanohydrins by (S)-hydroxynitrile lyase (Hevea brasiliensis) followed by lipase catalyzed kinetic resolution. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1990 / 1992
页数：3
相关论文
共 28 条
  • [1] Hydroxynitrile lyase catalysed synthesis of heterocyclic (R)- and (S)-cyanohydrins
    Avi, M
    Fechter, MH
    Gruber, K
    Bela, F
    Pöchlauer, P
    Griengl, H
    [J]. TETRAHEDRON, 2004, 60 (46) : 10411 - 10418
  • [2] Prunus Armeniaca Hydroxynitrile Lyase (ParHNL) Catalyzed Asymmetric Synthesis of δ,ε-Unsaturated Cyanohydrins
    Bhunya, Rajib
    Jana, Nandan
    Das, Tapas
    Nanda, Samik
    [J]. SYNLETT, 2009, (08) : 1237 - 1240
  • [3] Prunus armeniaca hydroxynitrile lyase (ParsHNL)-catalyzed asymmetric synthesis of cyanohydrins from sterically demanding aromatic aldehydes
    Bhunya, Rajib
    Mahapatra, Tridib
    Nanda, Samik
    [J]. TETRAHEDRON-ASYMMETRY, 2009, 20 (13) : 1526 - 1530
  • [4] 1-ARYL-2-(AMINOMETHYL)CYCLOPROPANECARBOXYLIC ACID-DERIVATIVES - A NEW SERIES OF POTENTIAL ANTIDEPRESSANTS
    BONNAUD, B
    COUSSE, H
    MOUZIN, G
    BRILEY, M
    STENGER, A
    FAURAN, F
    COUZINIER, JP
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (02) : 318 - 325
  • [5] C-C Bond-Forming Lyases in Organic Synthesis
    Brovetto, Margarita
    Gamenara, Daniela
    Saenz Mendez, Patricia
    Seoane, Gustavo A.
    [J]. CHEMICAL REVIEWS, 2011, 111 (07) : 4346 - 4403
  • [6] ASYMMETRIC SYNTHESES VIA CHIRAL ORGANOBORANE REAGENTS
    BROWN, HC
    JADHAV, PK
    MANDAL, AK
    [J]. TETRAHEDRON, 1981, 37 (21) : 3547 - 3587
  • [7] Carreira E.M., 2009, CLASSICS STEREOSELEC, P215
  • [8] Hydroxynitrile lyase-catalyzed addition of HCN to 4-substituted cyclohexanones:: stereoselective preparation of tetronic acids
    Effenberger, F
    Roos, J
    Kobler, C
    Bühler, H
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2002, 80 (06): : 671 - 679
  • [9] Effenberger F, 2002, ANGEW CHEM INT EDIT, V41, P1876, DOI 10.1002/1521-3773(20020603)41:11<1876::AID-ANIE1876>3.0.CO
  • [10] 2-1
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