Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 24, Pages 13677-13681Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202103910
Keywords
benzofuran; cascade catalysis; enantioselective hydrogenation; heterogeneous catalysis; homogeneous catalysis
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Funding
- Fonds der Chemischen Industrie
- Fulbright Germany
- Deutsche Forschungsgemeinschaft (Leibniz Award)
- European Research Council (ERC) [788558]
- Projekt DEAL
- European Research Council (ERC) [788558] Funding Source: European Research Council (ERC)
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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.
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.
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