A new route to 3,4-disubstituted piperidines: formal synthesis of (-)-paroxetine and (+)-femoxetine

被引：30
|
作者：
Yamada, S [1 ]
Jahan, I [1 ]
机构：
[1] Ochanomizu Univ, Dept Chem, Bunkyo Ku, Tokyo 1128610, Japan
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 50期
关键词：
(-)-paroxetine; (+)-femoxetine; face-selective addition; cation-pi interaction; 1,4-dihydropyridine;
D O I：
10.1016/j.tetlet.2005.10.049
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new route to 3,4-disubstituted piperidines was developed using chiral 1,4-dihydropyridines as key intermediates, the synthetic utility of which was demonstrated by formal synthesis of (-)-paroxetine and (+)-femoxetine. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：8673 / 8676
页数：4
相关论文
共 50 条
  • [1] Synthesis of enantiopure 3,4-disubstituted piperidines. An asymmetric synthesis of (+)-paroxetine
    Amat, M
    Hidalgo, J
    Bosch, J
    TETRAHEDRON-ASYMMETRY, 1996, 7 (06) : 1591 - 1594
  • [2] Synthesis of enantiopure trans-3,4-disubstituted piperidines.: An enantiodivergent synthesis of (+)- and (-)-paroxetine
    Amat, M
    Bosch, J
    Hidalgo, J
    Cantó, M
    Pérez, M
    Llor, N
    Molins, E
    Miravitlles, C
    Orozco, M
    Luque, J
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10): : 3074 - 3084
  • [3] A NEW ROUTE TO 3,4-DISUBSTITUTED TETRAHYDROTHIOPHENES
    ELALL, EHMA
    ALASHMAWY, MI
    MELLOR, JM
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (20) : 1577 - 1578
  • [4] SYNTHESES OF CERTAIN 3,4-DISUBSTITUTED PIPERIDINES
    KOELSCH, CF
    ROLFSON, ST
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (05) : 1871 - 1873
  • [5] Recent developments towards the synthesis of paroxetine: A 3,4-disubstituted piperidine
    Jana, Samaresh
    Sarkar, Sohini
    Morris, Scott A.
    TETRAHEDRON, 2020, 76 (25)
  • [6] Synthesis of new 3,4-disubstituted furazans
    Ivanova O.A.
    Averina E.B.
    Kuznetsova T.S.
    Zefirov N.S.
    Chemistry of Heterocyclic Compounds, 2000, 36 (09) : 1091 - 1096
  • [7] Synthesis of new 3,4-disubstituted furazanes
    Ivanova, OA
    Averina, EB
    Kuznetsova, TS
    Zefirov, NS
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2000, (09): : 1251 - 1258
  • [8] Zirconocene-mediated synthesis of 3,4-disubstituted piperidines and reduced isoquinolines
    Kemp, MI
    Whitby, RJ
    Coote, SJ
    SYNTHESIS-STUTTGART, 1998, : 557 - 568
  • [9] ZIRCONOCENE-MEDIATED SYNTHESIS OF 3,4-DISUBSTITUTED PIPERIDINES AND REDUCED ISOQUINOLINES
    KEMP, MI
    WHITBY, RJ
    COOTE, SJ
    SYNLETT, 1994, (06) : 451 - 453
  • [10] A novel and simple route for the synthesis of 3,4-disubstituted pyrroles
    Padmavathi, V
    Reddy, BJM
    Padmaja, A
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2005, 42 (02) : 333 - 335
12345