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Synthesis
DOI: 10.1055/a-2506-0261
DOI: 10.1055/a-2506-0261
paper
Novel Syntheses of rac- and Enantiomerically Enriched Dimethyl α-Methylphosphoserinate
The authors thank the Consejo Nacional de Humanidades, Ciencias y Tecnologías (CONAHCYT) for financial support (Projects 286614, 140607). E. B.-V. would like to thank CONAHCYT for a graduate scholarship (884123).
Abstract
The novel synthesis of racemic and enantiomerically enriched dimethyl (S)- and (R)-α-methylphosphoserinate is described. The racemic synthesis involves a three-component reaction of hydroxyacetone, benzylamine, dimethyl phosphite and catalytic amounts of phenylphosphonic acid, or alternatively, the reaction of ethyl pyruvate with NH4OAc and dimethyl phosphite in the presence of SiO2 under solvent-free conditions, followed by reduction of the ethyl ester with NaBH4 in THF/MeOH. On the other hand, the stereoselective synthesis includes the phosphonylation of chiral cyclic imines obtained by reaction of ethyl pyruvate with (S)- or (R)-phenylglycinol, followed by reduction of the cyclic ester with NaBH4 and cleavage of the phenylglycinol fragment under hydrogenolysis. The absolute configuration is established by 2D NOESY experiments. All synthesized compounds are fully characterized.
Key words
α-methylphosphoserinate - chiral cyclic imines - heterocyclic α-aminophosphonates - phosphonylationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2506-0261.
- Supporting Information
Publication History
Received: 04 December 2024
Accepted after revision: 18 December 2024
Accepted Manuscript online:
18 December 2024
Article published online:
11 February 2025
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