A Novel Strategy Towards Aminophosphonic Derivatives Based on the Diels-Alder Cycloaddition: Experimental and Theoretical Approaches

Abstract

this review focuses on the regio- and stereoselective synthesis of β-, γ-, and δ-aminophosphonic derivatives by combining dienophiles and dienes substituted by phosphono- and amino-groups. The initially formed cyclohexene adducts have been further transformed: chemoselective deprotections of masked P, C, and N functions, double bond oxidation and cleavage. Our Diels-Alder strategy has been successfully applied in asymmetric synthesis thanks to the development of a novel chiral 1-aminodiene designed by computational chemistry. The influence of a phosphonate substituent on reactivity in [4+2] cycloadditions has been theoretically studied. Keywords: diels-alder cycloaddition, vinyl phosphonates, phosphonodienes, aminodienes, asymmetric synthesis, ab initio methods