Conjugate Addition of Nitroalkanes to Nitroolefins

Significance

The reaction of both branched and unbranched nitroalkenes with aromatic nitroolefins catalyzed by demethylated quinidine is presented. Under neat conditions, a variety of 1,3-dinitro compounds is obtained in a Michael-type reaction. The products are typically obtained in good yields and moderate to good enantioselectivities. When linear, terminal nitroalkanes are employed (creating a second stereocenter in the same step), the achieved diastereoselectivities are modest. This is speculated to be partially due to rapid epimerization on the carbon attached to the nitro group. The reaction was found to be uninfluenced by both the sterical demand of the alkane and the electronic properties of the olefin. Aliphatic olefins, however, could not be successfully converted.