A Convenient Synthesis of γ-Amino-Ynamides via Additions of Lithiated Ynamides to Aryl Imines; Observation of an Aza-Meyer–Schuster Rearrangement

With the deepest respect and admiration, we dedicate this paper to Professor Scott E. Denmark on the very special occasion of his 60^th birthday.

Abstract

Efforts in developing an expeditious and convenient method for synthesizing γ-amino-ynamides via nucleophilic addition of lithiated ynamides to aryl imines are described. This work also features an aza-variant of a Meyer–Schuster rearrangement of γ-amino-ynamides and their synthetic utility in intramolecular ketenimine­ [2+2] cycloadditions.

Key words

lithiated ynamides - γ-amino-ynamides - aryl imines - azetene - aza-Meyer–Schuster rearrangement

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