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

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

Volume: 2 Issue: 4

Author(s): R. Robiette, N. Defacqz, D. Peeters and J. Marchand-Brynaert

Affiliation:

Keywords: diels-alder cycloaddition, vinyl phosphonates, phosphonodienes, aminodienes, asymmetric synthesis, ab initio methods

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.

Cite this article as:

Robiette R., Defacqz N., Peeters D. and Marchand-Brynaert J., A Novel Strategy Towards Aminophosphonic Derivatives Based on the Diels-Alder Cycloaddition: Experimental and Theoretical Approaches, Current Organic Synthesis 2005; 2 (4) . https://dx.doi.org/10.2174/157017905774322668