Synthesis Of Polycyclic Indoles Via Organocatalytic Bicyclization Of Alpha-Alkynylnaphthalen-2-Ols With Nitrones

A new organocatalytic bicyclization of alpha-alkynylnaphthalen-2-ols with nitrones was first reported, leading to the convergent synthesis of polycyclic indoles with substantial substitution diversity in generally good yields through scission of the N-O bond of nitronesvia[3,3]-sigmatropic rearrangement. This transformation showcases the use of a quinine catalyst in a complicated cascade system that has been shown to effectively construct polycyclic heterocyclesviaalkyne difunctionalization.