A Secondary Amine Amide Organocatalyst for the Asymmetric Nitroaldol Reaction of α-Ketophosphonates

Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University.
Chemistry - A European Journal (Impact Factor: 5.73). 12/2008; 14(35):10896-9. DOI: 10.1002/chem.200801958
Source: PubMed


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.

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