Enantioselective Synthesis of 2-Sulfenylated Aldehydes: Alkylation of Sulfenylated Acetaldehyde SAMP-Hydrazones

Article abstract of DOI:10.1016/S0040-4020(01)87015-0

A practical and efficient enantioselective synthesis of 2-sulfenylated aldehydes (S)-6 is described, based on the α-alkylation of sulfenylated acetaldehyde SAMP hydrazones (S)-4, easily prepared from bromoacetaldehyde diethylacetal 1, thiols and (S)-1-amino-2-methoxymethyl-pyrrolidine (SAMP).A chemoselective oxidative cleavage of the intermediate SAMP hydrazones (S,S)-5 with ozone gives rise to the title compounds (S)-6 in good overall yields and high enantiomeric excess of up to 97percent.