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Volumn 15, Issue 5, 2009, Pages 1227-1232

Enantioselective hydrogenation and transfer hydrogenation of bulky ketones catalysed by a ruthenium complex of a chiral tridentate ligand

Author keywords

Asymmetric catalysis; Heterocyclic ketones; Hydrogen transfer; Hydrogenation; N,P ligands

Indexed keywords

AMINES; CATALYSIS; ENANTIOSELECTIVITY; HYDROGEN; KETONES; LIGANDS; ORGANIC COMPOUNDS; RUTHENIUM; RUTHENIUM COMPOUNDS;

EID: 58449131526     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801929     Document Type: Article
Times cited : (73)

References (58)
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    • Some recent catalysts are based on significantly different co-ordination environments, and developments using such catalysts can be anticipated in the future. See: a
    • Some recent catalysts are based on significantly different co-ordination environments, and developments using such catalysts can be anticipated in the future. See: a) Y. J. Xu, N. W Alcock, G. J. Clarkson, G. Docherty, G. Woodward, M. Wills, Org. Lett. 2004, 6, 4105-4107;
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    • There are still no pressure hydrogenation catalysts capable of this task with any generality. However, a promising transfer hydrogenation system recently emerged: M. T. Reetz, X. Li, J. Am. Chem. Soc. 2006, 128, 1044-1045.
    • There are still no pressure hydrogenation catalysts capable of this task with any generality. However, a promising transfer hydrogenation system recently emerged: M. T. Reetz, X. Li, J. Am. Chem. Soc. 2006, 128, 1044-1045.
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    • While our work was in progress, the Noyori group reported the first Ru catalyst to show promise in hydrogenation of a few tertiary alkyl ketones. The catalyst is of the type [RuCl2(BINAP)picoline, T. Ohkuma, C. A. Sandoval, R. Srinivasan, Q. Lin, Y. Wei, K. Muniz, R. Noyori, J. Am. Chem. Soc. 2005, 127, 8288-8289
    • 2(BINAP)(picoline)]. T. Ohkuma, C. A. Sandoval, R. Srinivasan, Q. Lin, Y. Wei, K. Muniz, R. Noyori, J. Am. Chem. Soc. 2005, 127, 8288-8289.
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    • Imidazole-containing ketones were not hydrogenated by Noyori pressure hydrogenation, catalysts, although a transfer hydrogenation method was developed see
    • a) Imidazole-containing ketones were not hydrogenated by Noyori pressure hydrogenation, catalysts, although a transfer hydrogenation method was developed see: I. C Lennon, J. A. Ramsden, Org. Process Res. Dev. 2005, 9, 110-112;
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    • some pyridyl ketones require borate additives, see: T. Ohkuma, M. Koizumoi, M. Yoshida, R. Noyori, Org. Lett. 2000, 2, 1749-1751.
    • b) some pyridyl ketones require borate additives, see: T. Ohkuma, M. Koizumoi, M. Yoshida, R. Noyori, Org. Lett. 2000, 2, 1749-1751.
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    • A. promising Ru-based imine hydrogenation catalyst has been reported, but significant development is still needed: C. J. Cobley, J. P. Henschke, Adv. Synth. Catal. 2003, 345, 195-201;
    • a) A. promising Ru-based imine hydrogenation catalyst has been reported, but significant development is still needed: C. J. Cobley, J. P. Henschke, Adv. Synth. Catal. 2003, 345, 195-201;
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    • Some Ru ester hydrogenation catalysts based on tridentate ligands have been, reported: a) H. T. Teunissen and C. J. Elsevier, Chem. Commun. 1997, 667-668;
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    • triphosphine in asymmetric hydrogenation with (≈30% ee): P. Barbaro, C. Bianchini, G. Giambastiani, A. Togni, Eur. J. Inorg. Chem. 2003, 4166.
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    • Compound 1 has been reported before en-route to a tetradentate supported catalyst, see: S. Laue, L. Greiner, J. Woltinger, A. Liese, Adv. Synth. Catal. 2001, 343, 711-720. For a very interesting transfer hydrogenation catalyst based on the tetradentate analogue of catalyst 2
    • Compound 1 has been reported before en-route to a tetradentate supported catalyst, see: S. Laue, L. Greiner, J. Woltinger, A. Liese, Adv. Synth. Catal. 2001, 343, 711-720. For a very interesting transfer hydrogenation catalyst based on the tetradentate analogue of catalyst 2
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    • see: J. X. Gao, T. Ikariya, R. Noyori, Organometallies 1996, 15, 1087-1089. This catalyst gives poor selectivity in pressure hydrogenation; see ref. [19(a)].
    • see: J. X. Gao, T. Ikariya, R. Noyori, Organometallies 1996, 15, 1087-1089. This catalyst gives poor selectivity in pressure hydrogenation; see ref. [19(a)].
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    • For a recent domino synthesis of ketone 17, see: B. Willy, F. Rominger, T. J. J. Muller, Synthesis 2008, 293-303.
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    • Willy, B.1    Rominger, F.2    Muller, T.J.J.3
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    • some transfer hydrogenation catalysts are able to reduce bulky ketones. For reduction of 1,1′1″-trimethylacetophenone with similar ee, see: A. M. Hayes, D. J. Morris, G. J. Clarkson, M. Wills, J. Am. Chem. Soc. 2005, 127, 7318;
    • f) some transfer hydrogenation catalysts are able to reduce bulky ketones. For reduction of 1,1′1″-trimethylacetophenone with similar ee, see: A. M. Hayes, D. J. Morris, G. J. Clarkson, M. Wills, J. Am. Chem. Soc. 2005, 127, 7318;
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    • for transfer hydroge-nation, of imidazole-containing ketones in high ee, see: D. J. Morris, A. M. Hayes, M. Wills, J. Org. Chem. 2006, 71, 7035.
    • g) for transfer hydroge-nation, of imidazole-containing ketones in high ee, see: D. J. Morris, A. M. Hayes, M. Wills, J. Org. Chem. 2006, 71, 7035.
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    • A recent report by the Noyori group has described a transfer- hydrogenation catalyst that gave good results in pressure and hydrogenation; T. Ohkuma, N. Utsumi, K. Tsutsumi, K. Murata, C. Sandoval, R. Noyori, J. Am. Chem. Soc. 2006, 128, 8724-8725.
    • A recent report by the Noyori group has described a transfer- hydrogenation catalyst that gave good results in pressure and hydrogenation; T. Ohkuma, N. Utsumi, K. Tsutsumi, K. Murata, C. Sandoval, R. Noyori, J. Am. Chem. Soc. 2006, 128, 8724-8725.
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    • transfer hydrogenation using microwave heating using achiral catalyst: B. K. Bamik, K. J. Barakat, D. R. Wagle, M. S. Manhas, A. K. Bose, J. Org. Chem. 1999, 64, 5746-5753.
    • b) transfer hydrogenation using microwave heating using achiral catalyst: B. K. Bamik, K. J. Barakat, D. R. Wagle, M. S. Manhas, A. K. Bose, J. Org. Chem. 1999, 64, 5746-5753.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.