One-pot lipase-catalyzed synthesis of enantiopure secondary alcohols from carbonyl compounds: a new protocol for lipase-mediated resolution

被引:48
|
作者
Kamal, A [1 ]
Sandbhor, M [1 ]
Ramana, KV [1 ]
机构
[1] Indian Inst Chem Technol, Div Organ Chem, Biotransformat Lab, Hyderabad 500007, Andhra Pradesh, India
关键词
D O I
10.1016/S0957-4166(02)00170-2
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Reduction of acetophenones with sodium borohydride in the presence of neutral alumina in hexane followed by enantioselective acylation catalyzed by Pseudomonas cepacia lipase has been achieved in one-pot. Further, immobilized lipase offered a high degree of selectivity with spontaneity. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:815 / 820
页数:6
相关论文
共 50 条
  • [1] COMBINATION OF THE LIPASE-CATALYZED RESOLUTION WITH THE MITSUNOBU ESTERIFICATION IN ONE-POT
    VANTTINEN, E
    KANERVA, LT
    TETRAHEDRON-ASYMMETRY, 1995, 6 (07) : 1779 - 1786
  • [2] Synthesis of enantiopure monofluorinated phenylcyclopropanes by lipase-catalyzed kinetic resolution
    Rosen, TC
    Haufe, G
    TETRAHEDRON-ASYMMETRY, 2002, 13 (13) : 1397 - 1405
  • [3] Lipase-catalyzed kinetic resolution of large secondary alcohols having tetraphenylporphyrin
    Ema, T
    Jittani, M
    Sakai, T
    Utaka, M
    TETRAHEDRON LETTERS, 1998, 39 (35) : 6311 - 6314
  • [4] Toward one-pot lipase-catalyzed synthesis of poly(ε-caprolactone) particles in aqueous dispersion
    Inprakhon, Pranee
    Panlawan, Pabhangkon
    Pongtharankul, Thunyarat
    Marie, Emmanuelle
    Wiemann, Lars O.
    Durand, Alain
    Sieber, Volker
    COLLOIDS AND SURFACES B-BIOINTERFACES, 2014, 113 : 254 - 260
  • [5] One-pot synthesis of tetrahydrochromene derivatives catalyzed by lipase
    Xu, Jiang-Cheng
    Li, Wan-Mei
    Zheng, Hui
    Lai, Yi-Feng
    Zhang, Peng-Fei
    TETRAHEDRON, 2011, 67 (49) : 9582 - 9587
  • [6] LIPASE-CATALYZED KINETIC RESOLUTION WITH INSITU RACEMIZATION - ONE-POT SYNTHESIS OF OPTICALLY-ACTIVE CYANOHYDRIN ACETATES FROM ALDEHYDES
    INAGAKI, M
    HIRATAKE, J
    NISHIOKA, T
    ODA, J
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) : 9360 - 9361
  • [7] LIPASE-CATALYZED IRREVERSIBLE TRANSESTERIFICATION USING ENOL ESTERS - XAD-8 IMMOBILIZED LIPOPROTEIN LIPASE-CATALYZED RESOLUTION OF SECONDARY ALCOHOLS
    HSU, SH
    WU, SS
    WANG, YF
    WONG, CH
    TETRAHEDRON LETTERS, 1990, 31 (44) : 6403 - 6406
  • [8] Resolution of secondary alcohols via Carica papaya lipase-catalyzed enantioselective acylation
    Toshifumi Miyazawa
    Mika Houhashi
    Yusuke Inoue
    Takashi Murashima
    Takashi Yamada
    Biotechnology Letters, 2008, 30 : 1783 - 1787
  • [9] Resolution of secondary alcohols via Carica papaya lipase-catalyzed enantioselective acylation
    Miyazawa, Toshifumi
    Houhashi, Mika
    Inoue, Yusuke
    Murashima, Takashi
    Yamada, Takashi
    BIOTECHNOLOGY LETTERS, 2008, 30 (10) : 1783 - 1787
  • [10] Kinetic resolution of racemic secondary aliphatic allylic alcohols in lipase-catalyzed transesterification
    Chojnacka, Anna
    Obara, Robert
    Wawrzenczyk, Czeslaw
    TETRAHEDRON-ASYMMETRY, 2007, 18 (01) : 101 - 107