Organocatalysis for the Asymmetric Michael Addition of Aldehydes and α,β-Unsaturated Nitroalkenes

Michael addition is an important reaction because it can be used to synthesize a wide range of natural products or complex compounds that exhibit biological activities. In this study, mirror image aldehyde and α,β-unsaturated nitroalkene were reacted in the presence (R,R)-1,2-diphenylethylenediamine (DPEN). Herein, thiourea was introduced as organic catalyst, selective carried out. The primary amine moiety DPEN reacts with aldehydes form enamines, which activated by hydrogen bond formation between nitro groups nitroalkenes thiourea. Our aim obtain asymmetric product adding 1,4-enamine alkene new carbon–carbon bond. As result, chiral diamine converted enamine. proceeded relatively high degree enantioselectivity, achieved using double activation via bonding group enantioselectivity (97–99% synee) diastereoselectivity (syn/anti = 9/1) obtained yields ranging from 94–99% depending on aldehydes.