Chemoenzymatic synthesis of optically active 2-phenyl-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile

被引：28
|
作者：
Im, DS
Cheong, CS
Lee, SH
Youn, BH
Kim, SC
机构：
[1] Korea Inst Sci & Technol, Div Life Sci, Seoul 130650, South Korea
[2] Yonsei Univ, Dept Chem, Seoul 120749, South Korea
[3] Kook Min Univ, Dept Chem, Seoul 136702, South Korea
来源：
TETRAHEDRON | 2000年 / 56卷 / 10期
关键词：
chemoenzymatic; fungicide; quaternary carbon; lipase-catalyzed reaction;
D O I：
10.1016/S0040-4020(00)00031-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
(+/-)-2-Cyano-2-phenyl-1-hexanol 3 was resolved to each enantiomer using Candida rugosa and Pseudomonas fluorescens lipases in 62 and 99% ee, respectively. The absolute stereochemistry of one of the enantiomers was determined to be (S) by diastereomeric amide formation and X-ray crystallography. The resolved alcohols of (R)- and (S)-isomer were transformed to Systhane(R) analogues. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：1309 / 1314
页数：6
相关论文
共 50 条
  • [1] Synthesis and Genotoxicity of 4-(1H-Imidazol-1-ylmethyl)phenol and 4-(1H-1,2,4-Triazol-1-ylmethyl)phenol
    V. A. Osyanin
    E. S. Selezneva
    Z. P. Belousova
    L. F. Zarina
    N. E. Krel'
    P. P. Purygin
    Pharmaceutical Chemistry Journal, 2003, 37 (9) : 482 - 484
  • [2] 1,5-REARRANGEMENT OF ENOL ACYLATES OF ARYL 1H-1,2,4-TRIAZOL-1-YLMETHYL KETONES
    RADUL, OM
    KRIMER, MZ
    REBROVA, ON
    BIYUSHKIN, VN
    FEOFANOVA, IV
    PANASENKO, AA
    RUSSIAN CHEMICAL BULLETIN, 1993, 42 (03) : 522 - 527
  • [3] 4-(2-nitrobenzylideneamino)-3-(1H-1,2,4-triazol-1-ylmethyl)-1H-1,2,4-triazole-5(4H)-thione
    Lu, Xiao-Lan
    Bi, Wen-Zhao
    Shang, Yu-Qing
    Xu, Liang-Zhong
    Yu, Guan-Ping
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O3189 - O3190
  • [4] 4-(2-Hydroxybenzylideneamino)-3-(1H-1,2,4-triazol-1-ylmethyl)-1H-1,2,4-triazole-5(4H)-thione
    Hu, ZQ
    Shang, YQ
    Yu, GP
    Li, WH
    Xu, LZ
    Hou, BR
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : O3455 - O3456
  • [5] 4-(4-chlorobenzylideneamino)-3-(1H-1,2,4-triazol-1-ylmethyl)-1H-1,2,4-triazole-5(4H)-thione
    Xu, LZ
    Yu, GP
    Si, GD
    Shang, YQ
    Li, WH
    Hou, BR
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : O3408 - O3409
  • [6] catena-Poly[[diaquadichloridomanganese(II)]-μ-1,1′-bis(1H-1,2,4-triazol-1-ylmethyl)ferrocene]
    Shi, Chong-Yu
    Zhou, Xiao-Li
    Wu, Bo
    Zhu, Ni
    Weia, Zhen-Shu
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2010, 66 : M96 - U999
  • [7] 4-(3-Nitrobenzylideneamino)-3-(1H-1,2,4-triazol-1-ylmethyl)-1H-1,2,4-triazole-5(4H)-thione
    Shi, Xin-Yan
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : o1151 - o1152
  • [8] Synthesis, crystal structure and properties of the coordination polymer [HgI2(btx)]n (btx=1-[4-(1H-1,2,4-triazol-1-ylmethyl)benzyl]-1H-1,2,4-triazole)
    Xu, H
    Meng, XR
    Han, HY
    Wang, X
    Hou, HW
    CHINESE JOURNAL OF INORGANIC CHEMISTRY, 2004, 20 (09) : 1089 - 1092
  • [9] Synthesis and Crystal Structure of 2-(4-Fluoro-2-(4-fluorophenoxy)phenyl)-1-(1H-1,2,4-triazol-1-ylmethyl)-3-methoxy-isopropy Alcohol
    许良忠
    郭伟
    孙善起
    翟智卫
    Chinese Journal of Structural Chemistry, 2009, (08) : 963 - 966
  • [10] Synthesis and Crystal Structure of 2-(4-Fluoro-2-(4-fluorophenoxy)phenyl)-1-(1H-1,2,4-triazol-1-ylmethyl)-3-methoxy-isopropy Alcohol
    Xu Liang-Zhong
    Guo Wei
    Sun Shan-Qi
    Zhai Zhi-Wei
    CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2009, 28 (08) : 963 - 966
12345