C-benzylation of various sodium enolates derived frommethyl malonate, beta-ketoesters, a beta-cyanoester, a beta-cyanosulfone, ketones and a carboxylic ester is reported. Reaction of alkoxydiphenylsulfonium salts formed by treating various benzyl alcohols with diphenyl sulfide bis(trifluoromethanesulfonate) (derived from trifluoromethanesulfonic anhydride and diphenyl sulfoxide) proceeded smoothly, and
C-glycosides are synthesized in five steps starting from beta-C-glycosylaldehydes 1 and 2. The key step is a Pd(0)-catalyzed alkylation that leads regio and stereoselectively to exotic compounds by formation of C-C and C-N bonds. (C) 1997 Published by Elsevier Science Ltd.