ASYMMETRIC SULFENYLATION OF KETONES WITH CHIRAL SULFENAMIDES

Abstract

Abstract Asymmetric sulfenylations of 4-alkylcyclohexanones (6a,b) with chiral sulfenamides (1–5) were achieved in the presence of a catalytic amount of triethylamine hydrochloride to give 4-alkyl-2-phenylthiocyclohexanones (7a,b), which were transformed into optically active 4-alkyl-2-phenylthiocyclohexenes (10a,b) and 3-alkylcyclohexanones (11a,b) in fairly good chemical and optical yields. The influences of chiral sulfenamides and the reaction conditions on this asymmetric induction are described.