Stereocontrolled chemoenzymatic synthesis of 2,3-disubstituted piperidines

被引:22
作者
Monterde, MI [1 ]
Brieva, R [1 ]
Gotor, V [1 ]
机构
[1] Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, Oviedo 33006, Spain
关键词
D O I
10.1016/S0957-4166(01)00080-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
(R,R)-2,3-Disubstituted piperidines were readily synthesized starting from (R)-(+)- 5-bromo-2-hydroxypentanenitrile (R)-2. An enantioselective (R)-oxynitrilase-catalyzed transcyanation was used to prepare the starting cyanohydrin (R)-2. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:525 / 528
页数:4
相关论文
共 12 条
  • [1] Asymmetric routes to substituted piperidines
    Bailey, PD
    Millwood, PA
    Smith, PD
    [J]. CHEMICAL COMMUNICATIONS, 1998, (06) : 633 - 640
  • [2] BAKER R, Patent No. 9521819
  • [3] CARLIER P, Patent No. 2608603
  • [4] Synthesis of functionalized cyclic imines by addition of Grignard reagents to omega-bromonitriles and gamma,delta-unsaturated nitriles
    Fry, DF
    Brown, M
    McDonald, JC
    Dieter, RK
    [J]. TETRAHEDRON LETTERS, 1996, 37 (35) : 6227 - 6230
  • [5] FRY DF, 1994, SYNLETT, P836
  • [6] PIPERIDINE-ETHER BASED HNK(1) ANTAGONISTS .1. DETERMINATION OF THE RELATIVE AND ABSOLUTE STEREOCHEMICAL REQUIREMENTS
    HARRISON, T
    WILLIAMS, BJ
    SWAIN, CJ
    BALL, RG
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (21) : 2545 - 2550
  • [7] Laschat S, 2000, SYNTHESIS-STUTTGART, P1781
  • [8] OPTICALLY-ACTIVE (S)-KETONE-CYANOHYDRIN AND (R)-ALDEHYDE-CYANOHYDRIN VIA AN (R)-OXYNITRILASE-CATALYZED TRANSCYANATION - CHEMOENZYMATIC SYNTHESES OF 2-CYANOTETRAHYDROFURAN AND 2-CYANOTETRAHYDROPYRAN
    MENENDEZ, E
    BRIEVA, R
    REBOLLEDO, F
    GOTOR, V
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (10) : 989 - 990
  • [9] Chemoenzymatic synthesis of azacycloalkan-3-ols
    Monterde, MI
    Nazabadioko, S
    Rebolledo, F
    Brieva, R
    Gotor, V
    [J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (17) : 3449 - 3455
  • [10] Chemoenzymatic synthesis of (S)-2-cyanopiperidine, a key intermediate in the route to (S)-pipecolic acid and 2-substituted piperidine alkaloids
    Nazabadioko, S
    Pérez, RJ
    Brieva, R
    Gotor, V
    [J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (09) : 1597 - 1604