Lipase-catalyzed selective benzoylation of 1,2-diols with vinyl benzoate in organic solvents

被引:20
作者
Ciuffreda, P [1 ]
Alessandrini, L [1 ]
Terraneo, G [1 ]
Santaniello, E [1 ]
机构
[1] Univ Milan, Dipartimento Sci Preclin, LITA Vialba, I-20157 Milan, Italy
关键词
D O I
10.1016/j.tetasy.2003.07.003
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Lipases from Mucor miehei (MML) and Candida antarctica (CAL) are able to catalyze the benzoylation of the primary hydroxy group of 1.2-diols with vinyl benzoate in organic solvents. We have studied the MML-catalyzed benzoylation that proceeds with high regioselectivity and moderate enantioselectivity, whereas in the dibenzoylation reaction activity of MML and stereoselectivity of the enzymatic process is strongly influenced by steric factors. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3197 / 3201
页数:5
相关论文
共 30 条
[1]  
Andersch P, 1997, METHOD ENZYMOL, V286, P406
[2]   A convenient and practical method for the selective benzoylation of primary hydroxyl groups using microwave heating [J].
Caddick, S ;
McCarroll, AJ ;
Sandham, DA .
TETRAHEDRON, 2001, 57 (29) :6305-6310
[3]  
Carrea G, 2000, ANGEW CHEM INT EDIT, V39, P2226
[4]   ROLE OF SOLVENTS IN THE CONTROL OF ENZYME SELECTIVITY IN ORGANIC MEDIA [J].
CARREA, G ;
OTTOLINA, G ;
RIVA, S .
TRENDS IN BIOTECHNOLOGY, 1995, 13 (02) :63-70
[5]   QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].
CHEN, CS ;
FUJIMOTO, Y ;
GIRDAUKAS, G ;
SIH, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299
[6]   Lipase-catalyzed monoprotection of 1,4-diols in an organic solvent using vinyl benzoate as acyl transfer agent [J].
Ciuffreda, P ;
Casati, S ;
Santaniello, E .
TETRAHEDRON LETTERS, 2003, 44 (18) :3663-3665
[7]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[8]   ENZYMATIC-REACTIONS IN ORGANIC-SYNTHESIS .2. ESTER INTERCHANGE OF VINYL ESTERS [J].
DEGUEILCASTAING, M ;
DEJESO, B ;
DROUILLARD, S ;
MAILLARD, B .
TETRAHEDRON LETTERS, 1987, 28 (09) :953-954
[9]  
DRAUZ K, 1995, ENZYMES CATALYSIS OR
[10]   Kinetic resolution of racemic 2-substituted 3-cyclopenten-1-ols by lipase-catalyzed transesterifications: A rational strategy to improve enantioselectivity [J].
Ema, T ;
Maeno, S ;
Takaya, Y ;
Sakai, T ;
Utaka, M .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24) :8610-8616