Asymmetric Hydrogenation of Ketones with H2 and Ruthenium Catalysts Containing Chiral Tetradentate S2N2 Ligands†
Ruth Patchett
Corporate R&D Division, Firmenich SA route des Jeunes 1, P.O. Box 239, 1211 Genève 8 (Switzerland)
Search for more papers by this authorIris Magpantay
Corporate R&D Division, Firmenich SA route des Jeunes 1, P.O. Box 239, 1211 Genève 8 (Switzerland)
Search for more papers by this authorDr. Lionel Saudan
Corporate R&D Division, Firmenich SA route des Jeunes 1, P.O. Box 239, 1211 Genève 8 (Switzerland)
Search for more papers by this authorDr. Christoph Schotes
Department of Chemistry and Applied Biosciences, ETH Zürich, 8093 Zürich (Switzerland)
Search for more papers by this authorCorresponding Author
Prof. Dr. Antonio Mezzetti
Department of Chemistry and Applied Biosciences, ETH Zürich, 8093 Zürich (Switzerland)
Antonio Mezzetti, Department of Chemistry and Applied Biosciences, ETH Zürich, 8093 Zürich (Switzerland)
Francesco Santoro, Corporate R&D Division, Firmenich SA route des Jeunes 1, P.O. Box 239, 1211 Genève 8 (Switzerland)
Search for more papers by this authorCorresponding Author
Dr. Francesco Santoro
Corporate R&D Division, Firmenich SA route des Jeunes 1, P.O. Box 239, 1211 Genève 8 (Switzerland)
Antonio Mezzetti, Department of Chemistry and Applied Biosciences, ETH Zürich, 8093 Zürich (Switzerland)
Francesco Santoro, Corporate R&D Division, Firmenich SA route des Jeunes 1, P.O. Box 239, 1211 Genève 8 (Switzerland)
Search for more papers by this authorRuth Patchett
Corporate R&D Division, Firmenich SA route des Jeunes 1, P.O. Box 239, 1211 Genève 8 (Switzerland)
Search for more papers by this authorIris Magpantay
Corporate R&D Division, Firmenich SA route des Jeunes 1, P.O. Box 239, 1211 Genève 8 (Switzerland)
Search for more papers by this authorDr. Lionel Saudan
Corporate R&D Division, Firmenich SA route des Jeunes 1, P.O. Box 239, 1211 Genève 8 (Switzerland)
Search for more papers by this authorDr. Christoph Schotes
Department of Chemistry and Applied Biosciences, ETH Zürich, 8093 Zürich (Switzerland)
Search for more papers by this authorCorresponding Author
Prof. Dr. Antonio Mezzetti
Department of Chemistry and Applied Biosciences, ETH Zürich, 8093 Zürich (Switzerland)
Antonio Mezzetti, Department of Chemistry and Applied Biosciences, ETH Zürich, 8093 Zürich (Switzerland)
Francesco Santoro, Corporate R&D Division, Firmenich SA route des Jeunes 1, P.O. Box 239, 1211 Genève 8 (Switzerland)
Search for more papers by this authorCorresponding Author
Dr. Francesco Santoro
Corporate R&D Division, Firmenich SA route des Jeunes 1, P.O. Box 239, 1211 Genève 8 (Switzerland)
Antonio Mezzetti, Department of Chemistry and Applied Biosciences, ETH Zürich, 8093 Zürich (Switzerland)
Francesco Santoro, Corporate R&D Division, Firmenich SA route des Jeunes 1, P.O. Box 239, 1211 Genève 8 (Switzerland)
Search for more papers by this authorThe Authors thank Mr. Rino Schwenk for his assistance with the X-ray structure of complex 2 a and Dr. Alec Birkbeck for the generous donation of substrate 3 l.
Graphical Abstract
Getting more for less: In the presence of H2 and a base, air- and moisture-tolerant RuII complexes catalyze the hydrogenation of ketones and aldehydes with excellent activity and chemoselectivity, and with enantioselectivity of up to 95 % under mild conditions. The ratio of substrate to catalyst can be lowered to 106:1. The reactions tolerate scale-up and can be carried out with almost no solvent. A base-free method is available for base-sensitive substrates.
Supporting Information
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