Asymmetric Hydrogenation of Polysubstituted Aromatic Ketones Catalyzed by the DIPSkewphos/PICA Derivative-Ruthenium(II) Complexes
| Autor: | Kei Kawaguchi, Toshihisa Yasuda, Noriyuki Utsumi, Takeshi Ohkuma, Takeaki Katayama, Noriyoshi Arai, Kunihiko Murata |
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| Rok vydání: | 2018 |
| Předmět: |
Ketone
chemistry.chemical_element Alcohol 010402 general chemistry 01 natural sciences Medicinal chemistry Catalysis Inorganic Chemistry chemistry.chemical_compound medicine Pica (disorder) Physical and Theoretical Chemistry ruthenium chemistry.chemical_classification alcohol 010405 organic chemistry ketone Organic Chemistry Asymmetric hydrogenation Enantioselective synthesis asymmetric catalysis 0104 chemical sciences Ruthenium chemistry hydrogenation medicine.symptom Derivative (chemistry) |
| Zdroj: | ChemCatChem. 10:3955-3959 |
| ISSN: | 1867-3880 |
| DOI: | 10.1002/cctc.201800848 |
| Popis: | The DIPSkewphos/PICA derivative-Ru(II) complexes catalyzed asymmetric hydrogenation of significantly sterically hindered 2',3',4',5',6'-pentamethylacetophenone, which was not reduced with NaBH4 at 25 degrees C, with a substrate-to-catalyst molar ratio (S/C) of 2000 under 50 atm of H-2 in a base-containing 2-propanol to afford the alcohol in 99% ee quantitatively. A series of polysubstituted aromatic ketones was smoothly reacted with an S/C of 300-10,000 under 10-50 atm of H-2, yielding the alcoholic products in up to 99% ee. The catalyst system achieved an industrial-scale (50 kg) hydrogenation of 2',6'-dichloro-3'-fluoroacetophenone, affording the alcohol in 96% isolated yield and in 98% ee. The obtained alcoholic product is known as a key intermediate for the synthesis of the medicine crizotinib. |
| Databáze: | OpenAIRE |
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