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Asymmetric Hydrogenation of Polysubstituted Aromatic Ketones Catalyzed by the DIPSkewphos/PICA Derivative-Ruthenium(II) Complexes
| Title: | Asymmetric Hydrogenation of Polysubstituted Aromatic Ketones Catalyzed by the DIPSkewphos/PICA Derivative-Ruthenium(II) Complexes |
| Authors: | Utsumi, Noriyuki Browse this author | | Arai, Noriyoshi Browse this author | | Kawaguchi, Kei Browse this author | | Katayama, Takeaki Browse this author | | Yasuda, Toshihisa Browse this author | | Murata, Kunihiko Browse this author | | Ohkuma, Takeshi Browse this author →KAKEN DB |
| Keywords: | alcohol | | asymmetric catalysis | | hydrogenation | | ketone | | ruthenium |
| Issue Date: | 20-Sep-2018 |
| Publisher: | Wiley-Blackwell |
| Journal Title: | ChemCatChem |
| Volume: | 10 |
| Issue: | 18 |
| Start Page: | 3955 |
| End Page: | 3959 |
| Publisher DOI: | 10.1002/cctc.201800848 |
| Abstract: | 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. |
| Rights: | This is the peer reviewed version of the following article: ChemCatChem 10 (18) 3955-3959 2018-09-20, which has been published in final form at http://doi.org/10.1002/cctc.201800848. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/75497 |
| Appears in Collections: | 工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 大熊 毅
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