Treatment of ethanethiol esters with triethylsilane and palladium on carbon at ambient temperature furnished aldehydes. In addition, a variety of ketones have been prepared by a palladium-catalyzed reaction of ethanethiol esters with organozinc reagents. Various functional groups, including esters, ketones, aromatic halides and aldehydes, tolerate both transformation reactions. These novel reactions can also be applied to the synthesis of alpha-amino aldehyde and alpha-amino ketone derivatives using the corresponding L-alpha-amino thiol esters without causing racemization.
thiol ester; aldehyde; ketone; trietyl silane; organozinc reagent; palladium-catalyst
