A. Rzewnicka, J. Krysiak, M. Mikina
Jan 17, 2022
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Phosphorus, Sulfur, and Silicon and the Related Elements
Abstract
Abstract The synthesis of enantiomerically pure (1S,2S,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