Diastereoselective, One-Pot Synthesis of Polyfunctionalized Bicyclo[3.3.1]nonanes by an Anionic Domino Process

Diastereoselective, one-pot synthesis of polyfunctionalized bicyclo[3.3.1]nonanes from 1,3-dinitroalkanes and a commercially available ethyl(2-bromomethyl)-acrylate by an anionic domino process, was reported. The reactions were performed by adding the acylate to a solution of dinitroalkane under basic conditions, in acetonitrile, and at room temperature. It is noted that the target compounds are obtained as polyfunctionalized bicyclo[3.3.1]nonanes, since two tertiary nitro groups and two esters are present, giving the opportunity for further transformations. The results also show that a large collection of alkyl or aryl groups can be easily introduced in the 9-position, independent of their nature, by making an appropriate choice of the starting 1,3-dinitroalkanes.