Asymmetric synthesis of a cyclopropanecarboxylic acid derivative – the potential agonist/antagonist of GABA receptors. (22nd June 2022)

• Record Type: Journal Article
• Authors: Rzewnicka, Aneta; Krysiak, Jerzy; Mikina, Maciej; Żurawiński, Remigiusz; Sobczak, Agata; Sieroń, Lesław
• Is Part Of: Phosphorus, sulfur, and silicon and the related elements. Volume 197:Number 5/6(2022)
• Page Start: 593
• Page End: 596
• Publication Date: 2022-06-22
• Subjects: Cyclopropanes -- ylides -- amino acids -- cyclopropyl sulfoxide -- asymmetric synthesis; Sulfur compounds -- Periodicals; Organosulfur compounds -- Periodicals; Phosphorus compounds -- Periodicals; Organophosphorus compounds -- Periodicals; Silicon compounds -- Periodicals; Organosilicon compounds -- Periodicals; 546
• DOI: 10.1080/10426507.2021.2008931
• Languages: English
• ISSNs: 1042-6507

Abstract

Abstract: The synthesis of enantiomerically pure (1 S, 2 S, S P )-1-[hydroxy(methyl)phosphonyl]-2-aminocyclopropanecarboxylic acid (1 ) (a potential agonist/antagonist of GABA receptors) was accomplished in six steps based on optically inactive methyl 2-[methoxy(methyl)phosphonyl]acrylate (2 ). The key steps of this synthesis included the cyclopropane ring formation by the asymmetric cyclopropanation reaction of 2 with ( S )-dimethylsulfonium( p -tolylsulfinyl)methylide (3 ), regio and stereoselective installation of ethoxycarbonyl group in the cyclopropane ring, and the chemoselective desulfinylation reaction conducted with phenylsilane under the basic conditions. Graphical Abstract: UF0001