A new efficient protocol for diastereoselective three-component one-pot lactam synthesis involving in situ generation of imines via Staudinger/aza-Wittig tandem combined with Wolff-rearrangement and ketene-imine cycloaddition was developed to produce a...

Realization of the one-pot Staudinger/aza-Wittig/Castagnoli–Cushman reaction sequence for a series of azido aldehydes and homophthalic anhydrides is described. The reaction proceeded at room temperature and delivered novel polyheterocycles related to the natural product realm in high yields and high diastereoselectivity. The methodology has been extended to three other cyclic anhydrides. These further unravel the potential of the Castagnoli–Cushman reaction in generating polyheterocyclic molecular scaffolds.