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• W2024952052 startingPage "12648" @default.
• W2024952052 abstract "Contrary to the generally held view, it is found that the rapid epimerization of (-)-menthyl (RP)-phenylphosphinate under basic conditions is not due to the so far believed inherent stereolability of its corresponding anion but due to a reaction of the hydrogen phosphinate ester with a metal alkoxide. This finding successfully leads to a discovery that, by adding an H-phosphinate to organolithiums or Grignard reagents at a low temperature, the nucleophilic substitution of the alkoxy group of the H-phosphinate with organolithiums or Grignard reagents proceeds stereospecifically with inversion of configurations at phosphorus to give a wide range of P-stereogenic secondary phosphine oxides and tertiary phosphine oxides, by quenching the reaction mixture with water and alkyl halides, respectively. This finding establishes a general protocol for the preparation of optically active secondary phosphine oxides and tertiary phosphine oxides from the easily accessible optically pure H-phosphinates. Mechanistic studies show that the substitution reactions of H-phosphinates with organolithiums and Grignard reagents proceed via two competing reaction paths, that is, a two-step reaction path involving first a deprotonation of H-phosphinates followed by a substitution of the corresponding anion with inversion of configuration at phosphorus and a direct substitution of RM with H-phosphinates generating the SPO directly." @default.
• W2024952052 created "2016-06-24" @default.
• W2024952052 creator A5018744429 @default.
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• W2024952052 date "2008-08-30" @default.
• W2024952052 modified "2023-10-17" @default.
• W2024952052 title "Stereospecific Nucleophilic Substitution of Optically Pure <i>H</i>-Phosphinates: A General Way for the Preparation of Chiral P-Stereogenic Phosphine Oxides" @default.
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• W2024952052 doi "https://doi.org/10.1021/ja804412k" @default.
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