Influence of substituents on enantiomeric ratio in transesterification of racemic C-3 synthons using lipase B from Candida antarctica

The fluorides, chlorides and bromides of 3-halo-1-phenoxy-2-propanol, 3-halo-1-phenylmethoxy-2-propanol and 3-halo-1-(2-phenylethoxy)-2-propanol have been resolved by transesterification with various butanoates as acyl donors in hexane and lipase B from Candida antarctica (Novozyme 435) as catalyst. The enantiomeric ratio E depended on the hydroxy protecting groups in 1-position and the halogens in 3-position. For some substrates, the enantiomeric ratio was dependent on the acylating agent.