A molecular modelling approach to rationalize the stereochemical outcome of the Burkholderia cepacia lipase-catalyzed transesterification of aromatic primary alcohols with vinyl esters with different chain lengths in chloroform

Enzo Santaniello, Silvana Casati, Pierangela Ciuffreda, Giuseppe Meroni, Alessandro Pedretti, Giulio Vistoli

Research output: Contribution to journalArticle

Abstract

The Burkholderia cepacia lipase-catalyzed transesterification of 2-methyl-3-phenyl-1-propanol with vinyl esters proceeds with high enantioselectivity independently of the acyl chain length and the low enantioselectivity of the same reaction with 2-phenyl-1-propanol is not affected by chain length of the vinyl esters. A molecular modelling approach has been developed in order to rationalize the enzymatic results.

Original languageEnglish
Pages (from-to)1833-1836
Number of pages4
JournalTetrahedron: Asymmetry
Volume20
Issue number16
DOIs
Publication statusPublished - Aug 26 2009

ASJC Scopus subject areas

  • Organic Chemistry
  • Inorganic Chemistry
  • Physical and Theoretical Chemistry
  • Catalysis

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