(R)-2,3-cyclohexylideneglyceraldehyde, a chiral pool synthon for the synthesis of 2-azido-1,3-diols

Abstract

A new approach was proposed for the synthesis of 2-azido-1,3-diols from easily available and inexpensive chiral pool synthon (R)-2,3-O-cyclohexylidene-D-glyceraldehyde, through Mitsunobu azidation of 1,2-diols. Both C(2) and C(1) azides in variable ratios were obtained in alkyl substituted diols with C(2) as the major one.