The preparation of (R)-gamma-lactones was studied. The racemic homoallylic alcohols underwent kinetic resolution catalyzed by lipase CAL-B to give (R)-homoallylic alcohols and the corresponding acetates with S configuration. After 3 repeated resolutions, the ee values of the products exceeded 95% and the yields were about 40%. (S)-Acetates of homoallylic alcohols were converted to the opposite configuration in about 66% yield after hydrolysis and Mitsunobu reaction. (R)-Homoallylic alcohols reacted with acetic anhydride to produce the corresponding acetates in about 91% yield. (R)-Acetates of homoallylic alcohols were treated with borane in THF and CrO3 in acetic acid aqueous solution to give the intermediates, which were hydrolyzed and cyclized directly without purification to give (R)-gamma-lactones in about 72% yield with >94% ee.