Stereocontrolled Synthesis of Fluorine-Containing Piperidine γ-Amino Acid Derivatives

Ouchakour, Lamiaa and Ábrahámi, Renáta and Forró, Enikő and Haukka, Matti and Fülöp, Ferenc and Kiss, Loránd (2019) Stereocontrolled Synthesis of Fluorine-Containing Piperidine γ-Amino Acid Derivatives. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. ISSN 1434-193X

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Abstract

An efficient synthetic approach for the construction of fluorine-containing piperidine γ-amino acid derivatives has been developed. The synthetic concept was based on oxidative ring opening of an unsaturated bicyclic γ-lactam (Vince-lactam) through its ring C=C bond, followed by double reductive amination of the diformyl intermediate performed with various fluoroalkylamines. The method has been extended towards the access of alkylated and perfluoroalkylated substances and for γ-lactam derivatives. The transformations proceeded with stereocontrol: the configuration of the stereocenters in the products were predetermined by the configuration of the chiral centers of the starting γ-lactam. The method could be extended for the access to enantiopure piperidine γ-amino esters.

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