A general and practical approach for the synthesis of C-4 chiral building blocks using Jacobsen’s hydrolytic kinetic resolution technique to resolve terminal epoxides and diols in high enantiomeric excess and excellent yields is described. The utilization of these building blocks for the synthesis of biologically important natural products l-carnitine and α-lipoic acid is illustrated.
l-carnitine - α-lipoic acid - hydrolytic kinetic resolution - terminal epoxide - enantioenriched