Synthetic approach towards trisubstituted methanes and a chiral tertiary α-hydroxyaldehyde, a possible intermediate for tetrasubstituted methanes

A series of trisubstituted methanes containing aryl and heteroaryl rings, as well as a sulfur spacer between the central methano-carbon and benzene ring, is reported. In an approach towards asymmetric tetrasubstituted methane with high enantioselectivity, chiral tertiary α-hydroxyaldehyde has been synthesized through a Sharpless dihydroxylation on a disubstituted olefin, followed by the chemoselective oxidation of the primary alcohol.