Enantio- and Diastereoselective, Complete Hydrogenation of Benzofurans by Cascade Catalysis

We report an enantio- and diastereoselective, complete hydrogenation of multiply substituted benzofurans in a one-pot cascade catalysis. The developed protocol facilitates the controlled installation of up to six new defined stereocenters and produces architecturally complex octahydrobenzofurans, prevalent in many bioactive molecules. A unique match of a chiral homogeneous ruthenium-N-heterocyclic carbene complex and an in situ activated rhodium catalyst from a complex precursor act in sequence to enable the presented process.

Automated summary

This study presents a method for enantio- and diastereoselective hydrogenation of multiply substituted benzofurans in a one-pot cascade catalysis, allowing controlled installation of up to six new defined stereocenters to produce complex octahydrobenzofurans prevalent in bioactive molecules. The unique combination of a chiral homogeneous ruthenium-N-heterocyclic carbene complex and an in situ activated rhodium catalyst from a complex precursor enables the process.