Stereoselective conjugate addition of carbon nucleophiles to chiral (E)-nitroalkenes bearing a γ-stereocenter. Origins of the observed anti selectivity

Article abstract of DOI:10.1016/0040-4039(96)00468-6

The reaction between different organometallic carbon nucleophiles and chiral (E)-nitroalkenes has been studied. Anti selectivities have been observed in all cases. SCF-MO calculations suggest that the observed stereocontrol relies on the anti disposition of a donor group (methyl or hydrogen) with respect to the C-C bond in formation.