Enzyme-catalyzed resolution of aromatic ring fused cyclic tertiary alcohols

被引:25
|
作者
Ozdemirhan, Devrim [1 ]
Sezer, Serdar [2 ]
Sonmez, Yasemin [1 ]
机构
[1] Abant Izzet Baysal Univ, Dept Chem, TR-14280 Bolu, Turkey
[2] Middle E Tech Univ, Dept Chem, TR-06531 Ankara, Turkey
关键词
D O I
10.1016/j.tetasy.2008.12.002
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
An efficient chemoenzymatic route for the synthesis of optically active aromatic ring fused cyclic tertiary alcohols (S)-(-)-1-methyl-1,2,3,4-tetrahydronaphthalen-1-ol (-)-1b and (S)-(+)-1-methyl-2,3-dihydro-1H-inden-1-ol (+)-1a has been developed. Different lipases have been tested in the transesterification of these tertiary alcohols; CAL-A (Candida antarctica Lipase A) was found to be the best biocatalyst for 1b and CAL-A-CLEA (Lipase A, C. antarctica, cross-linked enzyme aggregate) for la, obtained with ee values of 20% and 45%, respectively, and the corresponding esters 2b and 2a with the ee values of 99% and 71%, respectively. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2717 / 2720
页数:4
相关论文
共 50 条
  • [1] Enzyme-catalyzed nucleophilic ring opening of Epoxides for the preparation of enantiopure tertiary alcohols
    Elenkov, Maja Majeric
    Hoeffken, H. Wolfgang
    Tang, Lixia
    Hauer, Bernhard
    Janssen, Dick B.
    ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (14-15) : 2279 - 2285
  • [2] Ruthenium and enzyme-catalyzed dynamic kinetic resolution of alcohols
    Karvembu, R.
    Prabhakaran, R.
    Tamizh, M. Muthu
    Natarajan, K.
    COMPTES RENDUS CHIMIE, 2009, 12 (09) : 951 - 962
  • [3] RESOLUTION OF SECONDARY ALCOHOLS BY ENZYME-CATALYZED TRANSESTERIFICATION IN ALKYL CARBOXYLATES AS THE SOLVENT
    JANSSEN, AJM
    KLUNDER, AJH
    ZWANENBURG, B
    TETRAHEDRON, 1991, 47 (36) : 7645 - 7662
  • [4] Ruthenium- and enzyme-catalyzed dynamic kinetic resolution of secondary alcohols
    Persson, BA
    Larsson, ALE
    Le Ray, M
    Bäckvall, JE
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (08) : 1645 - 1650
  • [5] Enzyme-catalyzed bioactivation of cyclic tertiary amines to form potential neurotoxins
    Castagnoli, N
    Castagnoli, KP
    Van der Schyf, CJ
    Usuki, E
    Igarashi, K
    Steyn, SJ
    Riker, RR
    POLISH JOURNAL OF PHARMACOLOGY, 1999, 51 (01): : 31 - 38
  • [6] Dynamic kinetic resolution of secondary alcohols combining enzyme-catalyzed transesterification and zeolite-catalyzed racemization
    Zhu, Yongzhong
    Fow, Kam-Loon
    Chuah, Gaik-Khuan
    Jaenicke, Stephan
    CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (02) : 541 - 547
  • [7] Enzyme-catalyzed asymmetric construction of chiral tertiary alcohols via aldol reaction using proteinase
    Li, Rui
    Li, Zhi-Lin
    Zhou, Hai-Yan
    He, Yan-Hong
    Guan, Zhi
    JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2016, 126 : 90 - 98
  • [8] Enzyme-catalyzed sulfide ring formation in lantibiotics
    Jung, Guenther
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (36) : 5919 - 5921
  • [9] ENZYME-CATALYZED RESOLUTION OF AMINO-ACIDS
    MOHRIG, JR
    SHAPIRO, SM
    JOURNAL OF CHEMICAL EDUCATION, 1976, 53 (09) : 586 - 589
  • [10] ENZYME-CATALYZED OXIDATION OF NONPHENOLIC AROMATIC-COMPOUNDS
    AGEORGES, A
    PELTER, A
    WARD, RS
    PHYTOCHEMISTRY, 1991, 30 (01) : 121 - 126