Ketenimine mediated synthesis of lactam iminosugars: development of one-pot process via tandem hydrative amidation of amino-alkynes and intramolecular transamidation

Cu-catalysed ketenimine mediated multicomponent reaction led to an efficient installation of N-allyl N-sulfonyl amide functionality onto a sugar derived terminal alkyne via intramolecular 3,3 sigmatropic rearrangement of an initially formed N-sulfonyl imidate. This strategy is further extended to the application of hydrative amide synthesis on chiral alkynyl amines followed by in situ intramolecular transamidation which led to the development of a novel one-pot reaction for the construction of a δ-lactam iminosugar.

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