ChemInform Abstract: New Highly Diastereoselective Synthesis of Phosphoramidates. A Route to Chiral Methyl p-Nitrophenyl Alkylphosphonates.

✍ Scribed by J.-F. CAVALIER; F. FOTIADU; R. VERGER; G. BUONO

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 36 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199821166

✦ Synopsis

New Highly Diastereoselective Synthesis of Phosphoramidates. A Route to Chiral Methyl p-Nitrophenyl Alkylphosphonates.

-Alkylphosphonic dichlorides such as (I) react successfully with L-proline ethyl ester and p-nitrophenol to afford phosphoramidates such as (IV) (interesting for biochemical investigations) with high diastereoselectivity. Methanolysis of (IV) occurs with complete inversion of the configuration at the phosphorus center leading to alkylphosphonates (VI). The ester group at the chiral auxiliary is found to be important for high-yielding reactions [cf. (VII)]. When other phenols such as (IX) are used extensive disubstitution is observed; however, the d.e. values of the desired products do not decrease. -(CAVALIER, J.-F.;