Gold-Catalyzed "Back-to-Front" Synthesis of 4-Silyloxyindoles.

ABSTRACT

A series of pyrrol-yn-glycol derivatives were easily prepared from simple pyrroles through a three-step sequence involving hydroxyalkylation-alkynylation-O-silylation. Their reaction with IPrAuNTf2 triggers a C2-pyrrole attack onto the activated alkyne and subsequent highly selective 1,2-migration of the oxyalkyl group in the intermediate spirocycle. This approach enables the efficient synthesis of a wide selection of regioselectively functionalized 4-hydroxyindoles, which represent important yet challenging indole scaffolds, in high yields.