Asymmetric synthesis employing chiral ketones as templates

Abstract

Synthesis of optically active α-alkyl and α-arylthioglycolic acids from thioglycolic acid could be achieved by employing (1R)-(+)-camphor as the template. Asymmetric synthesis of D-daunosamine from thioglycolic acid through chiral 1,3-oxathiolan-5-one 5a was achieved in six synthetic steps. Asymmetric synthesis of optically active 1,2-diols from alkynes through camphor derived chiral allenes is described. Preparation and synthetic application of chiral three carbon building blocks from glycerol could be achieved by employing (1S)-(+)-N,N-diisopropyl-10-camphorsulfonamide 2 as chiral template.