Preparation of Optically Active 2-Furylcarbinols by Kinetic Resolution Using the Sharpless Reagent and Their Application in Organic Synthesis

Article abstract of DOI:10.1021/jo00270a015

The kinetic resolution of 2-furylcarbinols 1 by the Sharpless reagent proceeds highly efficiently, thus providing a general method for the synthesis of homochiral 1.The reaction can be applied to compounds 1 possessing various types of substituents, although compound 1d, which has a sterically demanding tertiary alkyl group, is a poor substrate.The kinetic resolution of 3-furylcarbinol 3 also proceeds efficiently.Various homochiral 1 thus obtained have been successfully converted into α-alkoxy acids 4 by oxidative cleavage of the furan ring after protection of the hydroxyl group.The compound (R)-1b has been converted into the naturally occuring γ-lactone 5.