Efficient enantioselective syntheses of chloramphenicol and (d)-threo- and (d)-erythro-sphingosine

The chiral diazaborolidine 1 has been applied to the enantioselective syntheses of chloramphenicol (2) and (d)-threo-N-acetylsphingosine (3), a synthetic precursor of the diastereomeric (d)-sphingosines.