Regioselective Tandem <i>N</i>-Alkylation/<i>C</i>-Acylation of β,γ-Alkynyl α-Imino Esters

Abstract

A new synthesis of α-quaternary alkynyl amino esters and allenoates was developed utilizing umpolung N-addition to β,γ-alkynyl α-imino esters followed by regioselective acylation. The reaction exhibits broad substrate generality and unique regioselectivity. Moreover, synthesis of α-quaternary alkynyl amino esters was also carried out via oxidation of the intermediary enolate followed by alkylation.