Diastereoselective Synthesis of Enantiopure α-Aminophosphonic Acid Derivatives: Pudovik Reaction in Stereoselective Synthesis (Dedicated to A. N. Pudovik, 1916–2006)

Abstract

In this report, we present the application of Pudovik reaction in the synthesis of chiral organophosphorus compounds and shown this reaction to be a promising way to enantiopure aminophosphonic acid derivatives. Cyclization reactions are a new, most efficient strategy for stereoselective synthesis of α-aminophosphonates, namely an intramolecular type of interaction of the P(III) atom and an imino group.

Keywords:

• Cyclization reactions
• diastereoselectivity
• enantiopure α-aminophosphonates
• Pudovik reaction

Acknowledgments

This article was presented at the 17th International Conference on Phosphorus Chemistry (ICPC-17), April 15–21, 2007, Xiamen, China.

This work was supported by the Civilian Research and Development Foundation (grant no. RUC2-2638-KA-05) and the Russian Foundation for Basic Research (grant no. 07-03-00617).