Fluorinated iminophosphonates bearing stereodirecting phenylethyl group in synthesis of biorelevant scalemic aminophosphonates

Abstract

Diastereoselective reduction of α-(poly)fluoroalkylated iminophosphonates, bearing stereodirecting phenylethyl group at the nitrogen atom, produces diastereomeric N-(α-phenylethyl) polyfluoroalkylphosphonates. Separation and N-deprotection affords (S) and (R) α-amino polyfluoroalkylphosphonates. The latter react with 2,5-dimethoxytetrahydrofuran to give optically pure polyfluoroalkylphosphonates incorporating 1-pyrrolyl group in α-position.

Graphical Abstract

Keywords:

• Iminophosphonates
• optically active α-aminophosphonates
• polyfluoroalkylated aminophosphonic acids
• pyrroles