Preparation of dimethyl (R)- and (S)-2-(2-hydroxyphenyl)-2-hydroxyethylphosphonate derived from salicylaldehyde via resolution using (S)-methoxyphenylacetic acid (MPA) |
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| Affiliation: | 1. Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, 62209 Cuernavaca, Mor., Mexico;2. Unidad de Servicos de Apoyo en Resolución Analítica, Universidad Veracruzana, Av. Dr. Luis Castelazo Ayala s/n, 91190 Xalapa, Ver., Mexico |
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| Abstract: | The efficient preparation of both enantiomers of dimethyl δ,β-dihydroxyethylphosphonate 2 has been achieved from salicylaldehyde as a starting material, through the resolution of dimethyl (±)-2-(2-O-benzylphenyl)-2-hydroxyethylphosphonate 4 using (S)-methoxyphenylacetic acid (MPA). The absolute configuration was assigned by the Dale and Mosher approach using extended Newman projections and ab initio calculations. |
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