The reaction of propiolate acetylides with nitrones. Synthesis of γ-amino-α,β-ethylenic acid derivatives

Abstract

Nitrones react with the lithium anions of ethyl and t-butyl propiolates to give acetylenic N-hydroxylamines. The reduction of these compounds with Zn in the presence of an acid leads to E and Z α,β-ethylenic-γ-aminoacids derivatives. The stereoselectivity of these reactions was studied.