The Last Decade of Optically Active α-Aminophosphonates

Abstract

α-Aminophosphonates and related compounds are important due to their real and potential biological activity. α-Aminophosphonates may be prepared by the Kabachnik–Fields condensation of oxo compounds, amines and dialkyl phosphites, or by the aza-Pudovik addition of the same P-reagents to imines. In this review, the methods that allow for the synthesis of α-aminophosphonates with optical activity are surveyed. On the one hand, optically active catalysts or ligands may induce enantioselectivity during the Kabachnik–Fields reaction. On the other hand, asymmetric catalysis during the aza-Pudovik reaction, or hydrogenations of iminophosphonates, may prove to be a useful tool. Lastly yet importantly, it is possible to start from optically active reagents that may be associated with diastereoselectivity. The “green” aspects of the different syntheses are also considered.

Enantioselective synthesis of α-aryl α-hydrazino phosphonates

“… 2 α-Amino phosphonic acid derivatives, acting as amino acid mimics, are known to exhibit important biological activities such as antifungal, 3 antibacterial, 4 antioxidant, 5 anti-Alzheimer, 6 antiviral, 7 and anticancer activities, 8 among others. 9 Additionally, non-proteogenic α-hydrazino phosphonic acid derivatives, in which intramolecular H-bonds (hydrazino turns) 10 might modify their biological activities, have emerged as promising targets in medicinal chemistry. In particular, α-hydrazinophosphonate oxadiazoles I, 11 isatin derivatives II 12 and hydrazide III 4 a have been reported to exhibit promising activities against different types of cancer (I and II) and antimicrobial activity against K. Pneumonia (III) ( Fig.…”