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A stereodivergent and diastereoselective transition-metal-catalyzed intramolecular hydroamidation of allenes and alkynes furnishing δ-vinyl-lactams is reported. Employing a rhodium catalyst allowed for the selective synthesis of the syn -δ-lactam. Conversely, a palladium catalyst led to the formation of the anti -δ-lactam in high selectivity. The new method shows high functional group compatibility and assorted synthetic transformations were demonstrated as well as its utility for the enantioselective formal total syntheses of (-)-cermizine C and (-)-senepodine G.

chemical science

Transition metal catalyzed stereodivergent synthesis of <i>syn</i>- and <i>anti</i>-δ-vinyl-lactams: formal total synthesis of (−)-cermizine C and (−)-senepodine G

Transition metal catalyzed stereodivergent synthesis of syn- and anti-δ-vinyl-lactams: formal total synthesis of (−)-cermizine C and (−)-senepodine G