Optical resolution of 3-propionyloxy-1-trimethylsilyl-1-octyne or 3-(E)-propionyloxy-1-octene via lipase-mediated hydrolysis gave optically pure (S)-1-trimethylsilyl-1-octyn-3-ol and (R)- (E)-1-iodo-1-octen-3-ol, respectively, in which a reversal of enantio-selectivity for hydrolysis was observed between 3-propionyloxy-1-octyn and its 1-trimethylsilylated derivative, and the effect of the acyl groups on the enantio-discrimination was also investigated.
