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

[ Vol. 2 , Issue. 4 ]

Author(s):

R. Robiette, N. Defacqz, D. Peeters and J. Marchand-Brynaert   Pages 453 - 477 ( 25 )

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

Affiliation:

Universite catholique deLouvain, Departement de Chimie, Batiment Lavoisier, Place Louis Pasteur1, B-1348 Louvain-la-Neuve, Belgium.



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