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Volumn 7, Issue 6, 2005, Pages 1043-1045

Highly efficient iridium catalyst for asymmetric transfer hydrogenation of aromatic ketones under base-free conditions

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; BASE; IRIDIUM; IRIDIUM COMPLEX; KETONE DERIVATIVE; LIGAND; RHODIUM COMPLEX;

EID: 18244393749     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047412n     Document Type: Article
Times cited : (127)

References (31)
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    • For reviews on transfer hydrogenation, see: (a) Bäckvall, J.-E. J. Organomet. Chem. 2002, 652, 105. (b) Palmer, M. J.; Wills, M. Tetrahedron: Asymmetry 1999, 10, 2045. (c) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97. (d) Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051.
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    • For reviews on transfer hydrogenation, see: (a) Bäckvall, J.-E. J. Organomet. Chem. 2002, 652, 105. (b) Palmer, M. J.; Wills, M. Tetrahedron: Asymmetry 1999, 10, 2045. (c) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97. (d) Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051.
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    • Palmer, M.J.1    Wills, M.2
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    • For reviews on transfer hydrogenation, see: (a) Bäckvall, J.-E. J. Organomet. Chem. 2002, 652, 105. (b) Palmer, M. J.; Wills, M. Tetrahedron: Asymmetry 1999, 10, 2045. (c) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97. (d) Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051.
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    • Noyori, R.1    Hashiguchi, S.2
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    • For reviews on transfer hydrogenation, see: (a) Bäckvall, J.-E. J. Organomet. Chem. 2002, 652, 105. (b) Palmer, M. J.; Wills, M. Tetrahedron: Asymmetry 1999, 10, 2045. (c) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97. (d) Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051.
    • (1992) Chem. Rev. , vol.92 , pp. 1051
    • Zassinovich, G.1    Mestroni, G.2    Gladiali, S.3
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    • For transfer hydrogenation without bases: (a) Mizushima, E.; Yamaguchi, M.; Yamagishi, T. Chem. Lett. 1997, 237. (b) Eceraere, K.; Scheffler, J.-L.; Mortreux. A.; Carpentier, J.-F. Tetrahedron Lett. 2001, 42, 1899. (c) Cadierno, V.; Crochet, P.; Diez, J.; Garcia-Garrido, S. E.; Gimeno, J. Organometallics 2004, 23, 4836. (d) Dahlenburg, L.; Götz, R. Inorg. Chim. Acta 2004, 357, 2875. (e) For asymmetric transfer hydrogenation of acetophenone without bases with Ru complex: Haack, K.-J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285. (f) For asymmetric transfer hydrogenation of m-trifluoromethylacetophenone without bases: Murata, K.; Ikariya, T.; Noyori, R. J. Org. Chem. 1999, 64, 2186.
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  • 20
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    • For transfer hydrogenation without bases: (a) Mizushima, E.; Yamaguchi, M.; Yamagishi, T. Chem. Lett. 1997, 237. (b) Eceraere, K.; Scheffler, J.-L.; Mortreux. A.; Carpentier, J.-F. Tetrahedron Lett. 2001, 42, 1899. (c) Cadierno, V.; Crochet, P.; Diez, J.; Garcia-Garrido, S. E.; Gimeno, J. Organometallics 2004, 23, 4836. (d) Dahlenburg, L.; Götz, R. Inorg. Chim. Acta 2004, 357, 2875. (e) For asymmetric transfer hydrogenation of acetophenone without bases with Ru complex: Haack, K.-J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285. (f) For asymmetric transfer hydrogenation of m-trifluoromethylacetophenone without bases: Murata, K.; Ikariya, T.; Noyori, R. J. Org. Chem. 1999, 64, 2186.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 1899
    • Eceraere, K.1    Scheffler, J.-L.2    Mortreux, A.3    Carpentier, J.-F.4
  • 21
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    • For transfer hydrogenation without bases: (a) Mizushima, E.; Yamaguchi, M.; Yamagishi, T. Chem. Lett. 1997, 237. (b) Eceraere, K.; Scheffler, J.-L.; Mortreux. A.; Carpentier, J.-F. Tetrahedron Lett. 2001, 42, 1899. (c) Cadierno, V.; Crochet, P.; Diez, J.; Garcia-Garrido, S. E.; Gimeno, J. Organometallics 2004, 23, 4836. (d) Dahlenburg, L.; Götz, R. Inorg. Chim. Acta 2004, 357, 2875. (e) For asymmetric transfer hydrogenation of acetophenone without bases with Ru complex: Haack, K.-J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285. (f) For asymmetric transfer hydrogenation of m-trifluoromethylacetophenone without bases: Murata, K.; Ikariya, T.; Noyori, R. J. Org. Chem. 1999, 64, 2186.
    • (2004) Organometallics , vol.23 , pp. 4836
    • Cadierno, V.1    Crochet, P.2    Diez, J.3    Garcia-Garrido, S.E.4    Gimeno, J.5
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    • For transfer hydrogenation without bases: (a) Mizushima, E.; Yamaguchi, M.; Yamagishi, T. Chem. Lett. 1997, 237. (b) Eceraere, K.; Scheffler, J.-L.; Mortreux. A.; Carpentier, J.-F. Tetrahedron Lett. 2001, 42, 1899. (c) Cadierno, V.; Crochet, P.; Diez, J.; Garcia-Garrido, S. E.; Gimeno, J. Organometallics 2004, 23, 4836. (d) Dahlenburg, L.; Götz, R. Inorg. Chim. Acta 2004, 357, 2875. (e) For asymmetric transfer hydrogenation of acetophenone without bases with Ru complex: Haack, K.-J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285. (f) For asymmetric transfer hydrogenation of m-trifluoromethylacetophenone without bases: Murata, K.; Ikariya, T.; Noyori, R. J. Org. Chem. 1999, 64, 2186.
    • (2004) Inorg. Chim. Acta , vol.357 , pp. 2875
    • Dahlenburg, L.1    Götz, R.2
  • 23
    • 0030984352 scopus 로고    scopus 로고
    • For transfer hydrogenation without bases: (a) Mizushima, E.; Yamaguchi, M.; Yamagishi, T. Chem. Lett. 1997, 237. (b) Eceraere, K.; Scheffler, J.-L.; Mortreux. A.; Carpentier, J.-F. Tetrahedron Lett. 2001, 42, 1899. (c) Cadierno, V.; Crochet, P.; Diez, J.; Garcia-Garrido, S. E.; Gimeno, J. Organometallics 2004, 23, 4836. (d) Dahlenburg, L.; Götz, R. Inorg. Chim. Acta 2004, 357, 2875. (e) For asymmetric transfer hydrogenation of acetophenone without bases with Ru complex: Haack, K.-J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285. (f) For asymmetric transfer hydrogenation of m-trifluoromethylacetophenone without bases: Murata, K.; Ikariya, T.; Noyori, R. J. Org. Chem. 1999, 64, 2186.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 285
    • Haack, K.-J.1    Hashiguchi, S.2    Fujii, A.3    Ikariya, T.4    Noyori, R.5
  • 24
    • 0033515561 scopus 로고    scopus 로고
    • For transfer hydrogenation without bases: (a) Mizushima, E.; Yamaguchi, M.; Yamagishi, T. Chem. Lett. 1997, 237. (b) Eceraere, K.; Scheffler, J.-L.; Mortreux. A.; Carpentier, J.-F. Tetrahedron Lett. 2001, 42, 1899. (c) Cadierno, V.; Crochet, P.; Diez, J.; Garcia-Garrido, S. E.; Gimeno, J. Organometallics 2004, 23, 4836. (d) Dahlenburg, L.; Götz, R. Inorg. Chim. Acta 2004, 357, 2875. (e) For asymmetric transfer hydrogenation of acetophenone without bases with Ru complex: Haack, K.-J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285. (f) For asymmetric transfer hydrogenation of m-trifluoromethylacetophenone without bases: Murata, K.; Ikariya, T.; Noyori, R. J. Org. Chem. 1999, 64, 2186.
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    • Murata, K.1    Ikariya, T.2    Noyori, R.3
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    • note
    • 3). The mixture was stirred at 70°C for 30 min. To this solution was added the substrate (0.5 mmol), and the mixture was then stirred at the expected temperature. Samples were taken out of the reaction solution after the given time, passed through a column of silica, and analyzed by GC.


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