ENAMINES OF ACYLSILANES - ELECTROCHEMICAL SYNTHESIS, STRUCTURE, AND USE AS A SOURCE OF ALPHA-(TRIMETHYLSILYL)ALKYLAMINES

alpha-(Trimethylsilyl)alkylamines (''RSMA''), 1, have been prepared wi th good yields from enamines of acylsilanes, 2, through reduction of t he corresponding iminium salts, 5, with sodium borohydride. The entire process constitutes an original way to homologate a carbonyl compound into the next RSMA, as the starting enamine was obtained through redu ctive silylation of the O-silyl-protected cyanohydrin, 3, of this carb onyl compound. In this occasion, the electrochemical procedure for the reductive silylation was proven to be as effective as the chemical on e, giving 2 in yields of the same order of magnitude, Si-29 NMR spectr oscopic studies allowed the complete assignment of the E and Z structu res of these isomeric enamines.