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Volumn 29, Issue 24, 2010, Pages 6627-6631

Asymmetric hydrogenation of heteroaromatic compounds mediated by iridium-(P-OP) complexes

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC HYDROGENATION; HETEROAROMATIC COMPOUNDS; IRIDIUM COMPLEX; QUINOXALINES;

EID: 78650673887     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om100955t     Document Type: Article
Times cited : (61)

References (105)
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    • See, for example: Michael, J. P. Nat. Prod. Rep. 1997, 14, 605
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    • Hydrogenation of Imino Groups
    • See, for example, for general reviews on C = N hydrogenations: In Eds.; Springer-Verlag: Heidelberg, Germany
    • See, for example, for general reviews on C = N hydrogenations: Blaser, H.-U.; Spindler, F. Hydrogenation of Imino Groups. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, Germany, 1999; Vol. I, p 247.
    • (1999) Comprehensive Asymmetric Catalysis , vol.1 , pp. 247
    • Blaser, H.-U.1    Spindler, F.2    Jacobsen, E.N.3    Pfaltz, A.4    Yamamoto, H.5
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    • Pfaltz, A. Chimia 2001, 55, 708
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  • 49
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    • For asymmetric hydrogenations of isoquinolines, see, for example: For asymmetric hydrogenations of quinoxalines, see, for example: Heterocycles 1987, 26, 763
    • For asymmetric hydrogenations of isoquinolines, see, for example: Lu, S.-M.; Wang, Y.-Q.; Han, X.-W.; Zhou, Y.-G. Angew. Chem., Int. Ed. 2006, 45, 2260 For asymmetric hydrogenations of quinoxalines, see, for example: Murata, S.; Sugimoto, T.; Matsuura, S. Heterocycles 1987, 26, 763
    • (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 2260
    • Lu, S.-M.1    Wang, Y.-Q.2    Han, X.-W.3    Zhou, Y.-G.4    Murata, S.5    Sugimoto, T.6    Matsuura, S.7
  • 87
    • 78649509155 scopus 로고    scopus 로고
    • For examples of asymmetric hydrogenation of imines involving P-OP ligands, see refs 3j-3l; however, examples on the use of P-OP ligands in the asymmetric hydrogenation of heteroaromatic compounds are scarce (Rubio, M.; Pizzano, A. Molecules 2010, 15, 7732)
    • For examples of asymmetric hydrogenation of imines involving P-OP ligands, see refs 3j-3l; however, examples on the use of P-OP ligands in the asymmetric hydrogenation of heteroaromatic compounds are scarce (Rubio, M.; Pizzano, A. Molecules 2010, 15, 7732).
  • 88
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    • See the Supporting Information for full details
    • See the Supporting Information for full details.
  • 91
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    • This assumption was made on the basis of the coincidental NMR data (see the Supporting Information for details) for 5 and for 6 (whose structure was unequivocally elucidated by X-ray analysis)
    • This assumption was made on the basis of the coincidental NMR data (see the Supporting Information for details) for 5 and for 6 (whose structure was unequivocally elucidated by X-ray analysis).
  • 92
    • 0030739748 scopus 로고    scopus 로고
    • The steric environment at this position has proven critical to the catalytic activity of other chiral ligands derived from Sharpless epoxy alcohols, in several asymmetric transformations. See, for example
    • The steric environment at this position has proven critical to the catalytic activity of other chiral ligands derived from Sharpless epoxy alcohols, in several asymmetric transformations. See, for example: Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970
    • (1997) J. Org. Chem. , vol.62 , pp. 4970
    • Vidal-Ferran, A.1    Moyano, A.2    Pericas, M.A.3    Riera, A.4
  • 100
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    • For a general reference on additive effects, see: For details on specific additives, see: References 6u and 7c, for NBS
    • For a general reference on additive effects, see: Vogl, E. M.; Groger, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1999, 38, 1570 For details on specific additives, see: References 6u and 7c, for NBS.
    • (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 1570
    • Vogl, E.M.1    Groger, H.2    Shibasaki, M.3
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    • Reference 5a, for iodine
    • Reference 5a, for iodine.
  • 102
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    • Reference 7b, for TFA and p -toluenesulfonic and triflic acids
    • Reference 7b, for TFA and p -toluenesulfonic and triflic acids.
  • 103
    • 78650643851 scopus 로고    scopus 로고
    • Reference 5t, for camphorsulfonic acids
    • Reference 5t, for camphorsulfonic acids.
  • 104
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    • The use of ammonium or quinolinium chloride as additive has been reported by Feringa (6t) and Zhou. (7l) We chose adding anhydrous HCl (10 mol %) to generate in situ the corresponding hydrochloride of each substrate. Greater amounts of HCl (up to stoichiometric quantity) did not provide any improvement
    • The use of ammonium or quinolinium chloride as additive has been reported by Feringa (6t) and Zhou. (7l) We chose adding anhydrous HCl (10 mol %) to generate in situ the corresponding hydrochloride of each substrate. Greater amounts of HCl (up to stoichiometric quantity) did not provide any improvement.


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