A study was conducted for the asymmetric nitroaldol reaction of α-ketophosphonates by using a secondary amine amide organocatalyst. The study used a series of chiral secondary amine amides and synthesized it with α-ketophosphonates with nitromethane used as the solvent at 0°C. The nitroaldol reaction can be used for preparing nitrogen-containing compounds in the organic synthesis. It was observed during the study the α- ketophosphonates can be converted into optically active β-amino-α- hydroxy phosphonates, that further can be used as biological activity intermediates for inhibition of renin of HIV protease. The study also found that secondary amines like diethylamine or piperidine can promote the nitroaldol reaction of α-ketophosphonate at 0°C.
[Show abstract][Hide abstract] ABSTRACT: A series of C(3)-symmetric triprolinamide catalysts based on triphenyl- and tribenzylphosphine oxide has been developed to catalyze the direct asymmetric aldol reaction of aromatic aldehydes and cyclohexanone. Under the optimal conditions, high isolated yield (up to 96%), diastereoselectivities (up to 88:12) and enantioselectivities (up to 97%) were obtained.
[Show abstract][Hide abstract] ABSTRACT: The N,N'-dioxide-Sc(III) complex has been applied in the three-component Kabachnik-Fields reaction of aldehydes, 2-aminophenol, and diphenyl phosphite, giving the corresponding alpha-amino phosphonates in good yields with high enantioselectivities (up to 87% ee). The direct Kabachnik-Fields reaction proceeded with extremely high reactivity under mild reaction conditions and could be used for large-scale synthesis of the alpha-amino phosphonates.
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