title: Regioselective tandem N-alkylation/C-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.
authors.affiliation: Department of Chemistry for Materials, Graduate School of Engineering, Mie University, Tsu, Mie 514-8507, Japan.
authors.forename: Isao
authors.initials: I
authors.lastname: Mizota
authors.forename: Yuri
authors.initials: Y
authors.lastname: Matsuda
authors.forename: Satoshi
authors.initials: S
authors.lastname: Kamimura
authors.forename: Hirotaka
authors.initials: H
authors.lastname: Tanaka
authors.forename: Makoto
authors.initials: M
authors.lastname: Shimizu
mesh_terms: D000215:Acylation; D000478:Alkylation; D002384:Catalysis; D004952:Esters; D007098:Imino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D004952:Esters; D007098:Imino Acids