Nucleophilic (phenylsulfinyl)difluoromethylation of carbonyl compounds with difluoromethyl phenyl sulfoxide

We have successfully achieved nucleophilic (phenylsulfinyl)difluoromethylation of both enolizable and non-enolizable aldehydes and ketones by using difluoromethyl phenyl sulfone (1) as the fluoroalkylating agent. Although the chemical yields of the reactions are good to excellent, the observed diastereoselectivity is poor (dr = 1:1.04-2.03). The present synthetic methodology provides a convenient alternative for the preparation of alpha-(phenylsulfinyl)difluoromethylated carbinols that were previously synthesized via a two-step procedure. (C) 2007 Elsevier B.V. All rights reserved.