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

Abstract

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)-CH CH]-( l, d)-Ala and Boc-Phe -Ψ[( E)-CH CH]-( l, d)-Ala dipeptide isosters is also shown.