Substrate-oriented selectivity in the Mg-mediated conjugate addition of bromoform to electron-deficient alkenes.
Nishikant SatamSaumyadip NemuGuddeangadi N GururajaIrishi N N NamboothiriPublished in: Organic & biomolecular chemistry (2022)
The Mg-mediated conjugate addition of bromoform to a variety of electron-deficient alkenes has been investigated. In the case of nitrodienes and dibenzylideneacetones, tribromomethylated products were isolated, whereas spiro-cyclopropanated products were obtained with cyclic dibenzylideneketones and 3-olefinic oxindoles. The spiro-cyclopropyl ketones derived from cyclic dibenzylideneketones were successfully transformed into fused furans via the Cloke-Wilson rearrangement.