A novel strategy towards aminophosphonic derivatives based on the Diels-Alder cycloaddition: Experimental and theoretical approaches
(2005) Current Organic Synthesis — Vol. 2, n° 4, p. 453-477 (2005)
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- Abstract
- this review focuses on the regio- and stereoselective synthesis of beta-, gamma-, and delta-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.
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Citations
Robiette, R., Defacqz, N., Peeters, D., & Marchand-Brynaert, J. (2005). A novel strategy towards aminophosphonic derivatives based on the Diels-Alder cycloaddition: Experimental and theoretical approaches. Current Organic Synthesis, 2(4), 453-477. https://doi.org/10.2174/157017905774322668 (Original work published 2005)