Iridium Catalyzed Enantioselective Hydrogenation of Indole and Benzofuran Derivatives.

Enantioselective hydrogenation of a broad spectrum of N -, O -, and S -containing aromatic benzoheterocycles or nonaromatic unsaturated heterocycles has been reallized using an Ir/SpinPHOX complex as the catalyst under mild conditions affording an array of the corresponding chiral benzoheterocycles (30 examples) with nearly perfect optical purities (>99% ee in most cases) and a TON up to 500.