Selective lipase-catalyzed preparation of diol monobenzoates by transesterification and alcoholysis reactions in organic solvents |
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Authors: | Enzo Santaniello Pierangela Ciuffreda Silvana Casati Laura Alessandrini Alessandro Repetto |
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Affiliation: | aDipartimento di Scienze Precliniche LITA, Vialba-Università degli Studi di Milano, Via G.B. Grassi, 74-20157 Milano, Italy |
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Abstract: | Lipases from Mucor miehei (MML) and Candida antarctica (CAL) are able to catalyze the monobenzoylation of the primary hydroxy group of 1,2- 1,4- or 1,5-diols with vinyl benzoate in an organic solvent, the reaction proceeding with high regioselectivity and moderate enantioselectivity. The lipase-catalyzed debenzoylation of 1,2-propanediol dibenzoate by alcoholysis with 1-octanol most satisfactorily occurred with Pseudomonas cepacia lipase absorbed onto celite that allowed also to prepare (R)-1-benzoyloxy-2-methylpropan-3-ol from 2-methyl-1,3-propanediol dibenzoate, a result complementary to MML-catalyzed benzoylation of 2-methyl-1,3-propanediol that affords the (S)-monobenzoate. |
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Keywords: | Lipases Benzoylation Transesterification Alcoholysis Diols |
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