Stereoselective synthesis of dienylamines: from amino acids to E-alkene dipeptide isosters

A stereoselective approach to dienylamines is described, starting from enantiomerically enriched stannylated allylamines, which are in turn derived from amino acids. Conveniently the procedure allows to introduce diversity at 1-,2- and 4- positions of the final compounds. Conversion to vinylstannane has been extended to dipeptido aldehydes. The possible elaboration of 4-methyl substituted dienylamines to Boc-Gly-Ψ[(E)-CHdouble bond; length as m-dashCH]-(l,d)-Ala and Boc-Phe -Ψ[(E)-CHdouble bond; length as m-dashCH]-(l,d)-Ala dipeptide isosters is also shown.