A new class of organocatalysts involving a primary amine as the only functional group is developed for catalytic asymmetric aldol reaction of cyclohexanone/ cyclopentanone with various aryl aldehydes in thepresence of benzoic acid as an additive at −10◦C. In an unexpected observation, the primary amine catalyzed reactions gave excellent yield and good to excellent stereoselectivity, while secondary amines were found to have little or no reactivity under similar reaction conditions.

Organocatalytic asymmetric Michael addition is considered among the most extensively studied, yet challenging stereoselective reactions due to the fact that the electrophilic prochiral carbon in Michael acceptor lies away from stereodirecting groups of the catalyst. Although there is a report on stereoselective organocatalysis in Michael addition employing monofunctional secondary amine, the use of monofunctional primary amine forthe said reaction is not reported till date. In fact, no monofunctional aminocatalyst is reported yet for the synthesis γ-nitro carbonyl compounds. Here we report our preliminary results on the enantioselective Michael addition of different ketones to nitro olefins catalysed by monofunctional primary amine (1) derived from d-fructose.