Reductive Ring Opening of Arylcyclopropanecarboxamides Accompanied by Borylation and Enolate Formation.

Treatment of arylcyclopropanecarboxamides with a sodium dispersion in the presence of methoxypinacolborane as a reduction-resistant electrophile leads to reductive cleavage of the cyclopropane ring followed by instant trapping with the boron electrophile to yield the enolates of γ-aryl-γ-borylalkanamides. The enolates react further with a different electrophile to yield the corresponding α-substituted amides with anti selectivity.