Novel enzyme- and free radical-mediated reactions of oxirane derivatives

The thesis describes the use of various hydrolases in the preparation of enantiomerically enriched epoxyesters. Optically enriched n-butyl 4,5- epoxypentanoate was prepared with a 64% enantiomeric excess via the porcine pancreatic lipase-catalysed hydrolysis of the racemic ester. The hydrolase-catalysed hydrolysis of two prochiral epoxydiesters; meso 2,3-epoxybutan-1 A-diyl dibutanoate and 2,3-epoxy-2-butanoyloxymethylpropan-1-yl butanoate, were performed with several lipases, with the enantiomerically enriched epoxymonoesters being obtained in up to 80% and 65% enantiomeric excesses, respectively. Both isomers of the 4-butanoyloxy-2,3-epoxybutan-1-01 could be obtained via the hydrolysis of the diester by varying the lipase used. (2S, 3R)-4- Butanoyloxy-2,3-epoxybutan-1-01 was also isolated in up to 55% enantiomeric excess by the lipase-catalysed transesterification of vinyl butyrate with meso 2,3- epoxybutan-1 A-diol. [Continues.]