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Pseudomonas fluorescens lipase-catalyzed transesterification of 2-hydroxymethyl-1,4- benzodioxanes of different substitution patterns were studied in the presence of vinyl acetate in organic solvents. The influence of structural features on the conversion and enantioselectivity is discussed and it is shown that the presence of a C-3 methyl or aryl substituent significantly hinders the binding of the substrate to the active site of the enzyme. Thus, with a bulky C-3 substituent no transesterification of the 2-hydroxymethyl group could be observed.

Kinetic resolution of 2-hydroxymethyl-1,4-benzodioxanes by Pseudomonas fluorescens