Biocatalytic preparation of bicyclo[3.2.0]heptane derivatives

Abstract Bicyclo[3.2.0]hept-2-en-6-ols, central building blocks for the synthesis of chiral cyclobutane and -pentane systems, were prepared with up to >99% e.e. by lipase catalysed resolution of their acetates, butyrates, or isobutyrates. Substituents at C-7 vicinal to the reaction site reduced both enantioselectivity and reaction rate, whereas variation of the acid moiety showed a smaller influence. Among the lipase tested, those from Pseudomonas sp. were shown to be superior to those from Candida cylindracea, Mucor sp. and porcine pancreas.