Synthesis of tetrasubstituted nitroalkenes and preliminary studies of their enantioselective organocatalytic reduction.

Starting from commercially available ketones, a reproducible and reliable strategy for the
synthesis of tetrasubstituted nitroalkenes was successfully developed, using a two-step procedure;
the HWE olefination of the ketone to form the corresponding α,β-unsaturated esters is followed by a
nitration reaction to introduce the nitro group in the α position of the ester group. The enantioselective
organocatalytic reduction of these compounds has also been preliminarily studied, to access the
functionalized enantioenriched nitroalkanes, which are useful starting materials for further synthetic
elaborations. The absolute configuration of the reduction product was established by chemical
correlation of the chiral nitroalkane with a known product; preliminary DFT calculations were also
conducted to rationalize the stereochemical outcome of the organocatalytic enantioselective reduction.