Synthesis of chiral non-racemic 1,2-diamines from O-acetyl mandelic acid: application in enantioselective deprotonation of epoxides and diethylzinc addition to aldehydes

Abstract A variety of 1,2-diamines were synthesized from readily available O -acetyl mandelic acid. These diamines were used in the synthesis of key intermediates for the preparation of (−)-utenone A and carbovir involving enantioselective deprotonation of epoxides. The addition of Et 2 Zn catalysed by some of these diamines was also studied and although ees were not high, some interesting observations were made in the outcome of the stereochemistry of the product.