Lewis Acid Mediated Conjugate Addition of Isocyanides to β-Hydroxy-α-diazo Carbonyls: Synthesis of β-Carboxamido-α-diazo Carbonyl Compounds

A Lewis acid mediated conjugate addition of isocyanides to β-hydroxy-α-diazo carbonyls has been developed for the first time. The reaction realizes the efficient construction of quaternary carbon centers and provides a novel and efficient strategy for the synthesis of β-carboxamido-α-diazo carbonyls that would be otherwise difficult to form in a single step. Further applications, including synthesis of methylenecyclohexane, spiro-β-lactam, and nitrogen-bridged tricyclic β-lactam, demonstrated the tremendous potential of the coupling reaction.