Nitroaldol Reaction - Examples


Industrial Application- In 1999, Menzel and coworkers developed a synthetic route to obtaining L-Acosamine, the carbohydrate subunit of the anthracycline class of antibiotics

Industrial Application- An enantioselective aldol addition product can be obtained in asymmetric synthesis by reaction of benzaldehyde with nitromethane and the a catalyst system consisting of a zinc triflate salt / the base diisopropylethylamine (DIPEA) and as chiral ligand is the N-methyl derivative of (+)-ephedrine (NME).

A diastereoselective variation of this reaction is depicted below.

Total Synthesis- In 2005, Barua and coworkers completed the total synthesis of the potent aminopeptidase inhibitor, (-)-bestatin, in an overall yield of 26% overall yield employing Shisasaki's asymmetric Henry reaction as the key step. (illustrated below)

Organocatalysis- In 2006, Hiemstra and coworkers explored the use of quinine derivatives as asymmetric catalysts for the reaction between aromatic aldehydes and nitromethane. Through the use of particular derivatives, they were able to induce direct enantioselection through the use of the proper catalyst.

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