Construction of 4-substituted 2-(pyrrolidine-3-yl)acetic acid derivatives as cyclic gamma-aminobutyric acid analogues employing intermolecular [2+2]-photocycloaddition as key steps

Petz, Susanne; Allmendinger, Lars; Mayer, Peter and Wanner, Klaus T. (2019): Construction of 4-substituted 2-(pyrrolidine-3-yl)acetic acid derivatives as cyclic gamma-aminobutyric acid analogues employing intermolecular [2+2]-photocycloaddition as key steps. In: Tetrahedron, Vol. 75, No. 19: pp. 2755-2762

Abstract

The synthesis of new 2-(pyrrolidine-3-yl)acetic acid derivatives as cyclic gamma-aminobutyric acid analogues, which are additionally substituted at the 4-position, is reported. A de Mayo reaction, i.e. a combination of an intermolecular [2+2]-photocycloaddition of 1,3-dioxinones with N-protected 3-pyrroline and a fragmentation reaction of the resulting cyclobutane moiety, represent the key steps. (C) 2019 Elsevier Ltd. All rights reserved.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 0040-4020
• Language: English