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Volumn 21, Issue 22, 2002, Pages 4611-4621

Electronic differences between coordinating functionalities of chiral phosphine-phosphites and effects in catalytic enantioselective hydrogenation

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL BONDS; COMPLEXATION; HYDROGENATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL);

EID: 0038676301     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om020140c     Document Type: Article
Times cited : (120)

References (56)
  • 5
    • 37049084227 scopus 로고
    • P-N ligands
    • See for instance; P-N ligands: Alcock, N.; Hulmes, D. I.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1995, 395. Wimmer, P.; Wildham, M. Tetrahedron: Asymmetry 1995, 6, 657. P-O ligands: Nandy, M.; Jin, J.; RajanBabu, T. V. J. Am. Chem. Soc. 1999, 121, 9899. Uozumi, Y.; Tanahashi, A.; Lee, S.-Y.; Hayashi, T. J. Org. Chem. 1993, 58, 1945. P-S ligands: Hauptman, E.; Fagan, P. J.; Marshall, W. Organometallics 1999, 18, 2061. P-P′ ligands: Ireland, T.; Grossheimann, G.; Wieser-Jeunesse, C.; Knochel, P. Angew. Chem., Int. Ed. 1999, 38, 3212. Ohashi, A.; Imamoto, T. Tetrahedron Lett. 2001, 42, 1099. Tanaka, K.; Fu, G. C. J. Org. Chem. 2001, 66, 8177.
    • (1995) J. Chem. Soc., Chem. Commun. , pp. 395
    • Alcock, N.1    Hulmes, D.I.2    Brown, J.M.3
  • 6
    • 0028920120 scopus 로고
    • See for instance; P-N ligands: Alcock, N.; Hulmes, D. I.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1995, 395. Wimmer, P.; Wildham, M. Tetrahedron: Asymmetry 1995, 6, 657. P-O ligands: Nandy, M.; Jin, J.; RajanBabu, T. V. J. Am. Chem. Soc. 1999, 121, 9899. Uozumi, Y.; Tanahashi, A.; Lee, S.-Y.; Hayashi, T. J. Org. Chem. 1993, 58, 1945. P-S ligands: Hauptman, E.; Fagan, P. J.; Marshall, W. Organometallics 1999, 18, 2061. P-P′ ligands: Ireland, T.; Grossheimann, G.; Wieser-Jeunesse, C.; Knochel, P. Angew. Chem., Int. Ed. 1999, 38, 3212. Ohashi, A.; Imamoto, T. Tetrahedron Lett. 2001, 42, 1099. Tanaka, K.; Fu, G. C. J. Org. Chem. 2001, 66, 8177.
    • (1995) Tetrahedron: Asymmetry , vol.6 , pp. 657
    • Wimmer, P.1    Wildham, M.2
  • 7
    • 0033610498 scopus 로고    scopus 로고
    • P-O ligands
    • See for instance; P-N ligands: Alcock, N.; Hulmes, D. I.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1995, 395. Wimmer, P.; Wildham, M. Tetrahedron: Asymmetry 1995, 6, 657. P-O ligands: Nandy, M.; Jin, J.; RajanBabu, T. V. J. Am. Chem. Soc. 1999, 121, 9899. Uozumi, Y.; Tanahashi, A.; Lee, S.-Y.; Hayashi, T. J. Org. Chem. 1993, 58, 1945. P-S ligands: Hauptman, E.; Fagan, P. J.; Marshall, W. Organometallics 1999, 18, 2061. P-P′ ligands: Ireland, T.; Grossheimann, G.; Wieser-Jeunesse, C.; Knochel, P. Angew. Chem., Int. Ed. 1999, 38, 3212. Ohashi, A.; Imamoto, T. Tetrahedron Lett. 2001, 42, 1099. Tanaka, K.; Fu, G. C. J. Org. Chem. 2001, 66, 8177.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 9899
    • Nandy, M.1    Jin, J.2    Rajanbabu, T.V.3
  • 8
    • 0001514035 scopus 로고
    • See for instance; P-N ligands: Alcock, N.; Hulmes, D. I.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1995, 395. Wimmer, P.; Wildham, M. Tetrahedron: Asymmetry 1995, 6, 657. P-O ligands: Nandy, M.; Jin, J.; RajanBabu, T. V. J. Am. Chem. Soc. 1999, 121, 9899. Uozumi, Y.; Tanahashi, A.; Lee, S.-Y.; Hayashi, T. J. Org. Chem. 1993, 58, 1945. P-S ligands: Hauptman, E.; Fagan, P. J.; Marshall, W. Organometallics 1999, 18, 2061. P-P′ ligands: Ireland, T.; Grossheimann, G.; Wieser-Jeunesse, C.; Knochel, P. Angew. Chem., Int. Ed. 1999, 38, 3212. Ohashi, A.; Imamoto, T. Tetrahedron Lett. 2001, 42, 1099. Tanaka, K.; Fu, G. C. J. Org. Chem. 2001, 66, 8177.
    • (1993) J. Org. Chem. , vol.58 , pp. 1945
    • Uozumi, Y.1    Tanahashi, A.2    Lee, S.-Y.3    Hayashi, T.4
  • 9
    • 0000840517 scopus 로고    scopus 로고
    • P-S ligands
    • See for instance; P-N ligands: Alcock, N.; Hulmes, D. I.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1995, 395. Wimmer, P.; Wildham, M. Tetrahedron: Asymmetry 1995, 6, 657. P-O ligands: Nandy, M.; Jin, J.; RajanBabu, T. V. J. Am. Chem. Soc. 1999, 121, 9899. Uozumi, Y.; Tanahashi, A.; Lee, S.-Y.; Hayashi, T. J. Org. Chem. 1993, 58, 1945. P-S ligands: Hauptman, E.; Fagan, P. J.; Marshall, W. Organometallics 1999, 18, 2061. P-P′ ligands: Ireland, T.; Grossheimann, G.; Wieser-Jeunesse, C.; Knochel, P. Angew. Chem., Int. Ed. 1999, 38, 3212. Ohashi, A.; Imamoto, T. Tetrahedron Lett. 2001, 42, 1099. Tanaka, K.; Fu, G. C. J. Org. Chem. 2001, 66, 8177.
    • (1999) Organometallics , vol.18 , pp. 2061
    • Hauptman, E.1    Fagan, P.J.2    Marshall, W.3
  • 10
    • 0033517686 scopus 로고    scopus 로고
    • P-P′ ligands
    • See for instance; P-N ligands: Alcock, N.; Hulmes, D. I.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1995, 395. Wimmer, P.; Wildham, M. Tetrahedron: Asymmetry 1995, 6, 657. P-O ligands: Nandy, M.; Jin, J.; RajanBabu, T. V. J. Am. Chem. Soc. 1999, 121, 9899. Uozumi, Y.; Tanahashi, A.; Lee, S.-Y.; Hayashi, T. J. Org. Chem. 1993, 58, 1945. P-S ligands: Hauptman, E.; Fagan, P. J.; Marshall, W. Organometallics 1999, 18, 2061. P-P′ ligands: Ireland, T.; Grossheimann, G.; Wieser-Jeunesse, C.; Knochel, P. Angew. Chem., Int. Ed. 1999, 38, 3212. Ohashi, A.; Imamoto, T. Tetrahedron Lett. 2001, 42, 1099. Tanaka, K.; Fu, G. C. J. Org. Chem. 2001, 66, 8177.
    • (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 3212
    • Ireland, T.1    Grossheimann, G.2    Wieser-Jeunesse, C.3    Knochel, P.4
  • 11
    • 0035808963 scopus 로고    scopus 로고
    • See for instance; P-N ligands: Alcock, N.; Hulmes, D. I.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1995, 395. Wimmer, P.; Wildham, M. Tetrahedron: Asymmetry 1995, 6, 657. P-O ligands: Nandy, M.; Jin, J.; RajanBabu, T. V. J. Am. Chem. Soc. 1999, 121, 9899. Uozumi, Y.; Tanahashi, A.; Lee, S.-Y.; Hayashi, T. J. Org. Chem. 1993, 58, 1945. P-S ligands: Hauptman, E.; Fagan, P. J.; Marshall, W. Organometallics 1999, 18, 2061. P-P′ ligands: Ireland, T.; Grossheimann, G.; Wieser-Jeunesse, C.; Knochel, P. Angew. Chem., Int. Ed. 1999, 38, 3212. Ohashi, A.; Imamoto, T. Tetrahedron Lett. 2001, 42, 1099. Tanaka, K.; Fu, G. C. J. Org. Chem. 2001, 66, 8177.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 1099
    • Ohashi, A.1    Imamoto, T.2
  • 12
    • 0035977219 scopus 로고    scopus 로고
    • See for instance; P-N ligands: Alcock, N.; Hulmes, D. I.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1995, 395. Wimmer, P.; Wildham, M. Tetrahedron: Asymmetry 1995, 6, 657. P-O ligands: Nandy, M.; Jin, J.; RajanBabu, T. V. J. Am. Chem. Soc. 1999, 121, 9899. Uozumi, Y.; Tanahashi, A.; Lee, S.-Y.; Hayashi, T. J. Org. Chem. 1993, 58, 1945. P-S ligands: Hauptman, E.; Fagan, P. J.; Marshall, W. Organometallics 1999, 18, 2061. P-P′ ligands: Ireland, T.; Grossheimann, G.; Wieser-Jeunesse, C.; Knochel, P. Angew. Chem., Int. Ed. 1999, 38, 3212. Ohashi, A.; Imamoto, T. Tetrahedron Lett. 2001, 42, 1099. Tanaka, K.; Fu, G. C. J. Org. Chem. 2001, 66, 8177.
    • (2001) J. Org. Chem. , vol.66 , pp. 8177
    • Tanaka, K.1    Fu, G.C.2
  • 22
    • 33847090571 scopus 로고
    • Several methods have been used for the synthesis of diverse phenol phosphines. For representative procedures see: (a) Rauchfuss, T. B. Inorg. Chem. 1977, 16, 2966.
    • (1977) Inorg. Chem. , vol.16 , pp. 2966
    • Rauchfuss, T.B.1
  • 25
    • 0034612942 scopus 로고    scopus 로고
    • Only recently, Jugé and co-workers have described the first enantioselective synthesis of a P-stereogenic 2-hydroxyaryl phosphine ((R)-o-anisyl-2-hydroxynaphthylphenyl phosphine) using an alternative procedure; however, this method requires difficultly accessible enantiopure phosphinite boranes: Moulin, D.; Bago, S.; Bauduin, C.; Darcel, C.; Jugé, S. Tetrahedron: Asymmetry 2000, 11, 3939.
    • (2000) Tetrahedron: Asymmetry , vol.11 , pp. 3939
    • Moulin, D.1    Bago, S.2    Bauduin, C.3    Darcel, C.4    Jugé, S.5
  • 26
    • 0001651724 scopus 로고
    • This sequence of reactions has been used previously in the synthesis of some quinolyl phosphines: Sembiring, S. B.; Colbran, S. B.; Craig, D. C. Inorg. Chem. 1995, 34, 761.
    • (1995) Inorg. Chem. , vol.34 , pp. 761
    • Sembiring, S.B.1    Colbran, S.B.2    Craig, D.C.3
  • 33
    • 0038739677 scopus 로고    scopus 로고
    • note
    • 3 P=Se also exhibited a lower coupling constant value than expected (712 Hz, ref 15).
  • 35
    • 0000251150 scopus 로고    scopus 로고
    • The magnitude of this parameter has been amply used as a measure of the electron density at a metal center; for a recent application see: Serron, S.; Huang, J.; Nolan, S. P. Organometallics 1998, 17, 534.
    • (1998) Organometallics , vol.17 , pp. 534
    • Serron, S.1    Huang, J.2    Nolan, S.P.3
  • 36
    • 0001019566 scopus 로고
    • PRh has been widely used as a structural tool in the analysis of rhodium complexes. The magnitude of this parameter depends markedly on the ligand situated in the trans position with respect to the phosphine/phosphite ligand, being larger for a phosphorus trans to chloride than to a carbonyl ligand. See for instance: Naaktgeboren, A. J.; Nolte, R. J. M.; Drenth, W. J. Am. Chem. Soc. 1980, 102, 3350.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 3350
    • Naaktgeboren, A.J.1    Nolte, R.J.M.2    Drenth, W.3
  • 41
    • 0003400107 scopus 로고
    • John Wiley and Sons: New York
    • This distribution is observed in a great number of bis aryl phosphines with a chiral backbone, see for instance: Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley and Sons: New York, 1994.
    • (1994) Asymmetric Catalysis in Organic Synthesis
    • Noyori, R.1
  • 43
    • 0038063200 scopus 로고    scopus 로고
    • note
    • We have noted a rather low reactivity of 9a toward hydrogen compared with diphosphine-based catalyst precursors. This observation is in good agreement with the behavior described for other phosphine-phosphite derivatives (ref 6d) and could be adscribed to the rather low donating ability of ligands 5.
  • 46
    • 0038401491 scopus 로고    scopus 로고
    • note
    • Recently, Claver and van Leeuwen have proposed the same coordination mode for a derivative of a phosphine - phosphite: ref 6c.
  • 49
    • 0038739676 scopus 로고    scopus 로고
    • note
    • The structure of dihydrides K and K′ has been proponed by similarity with those described in ref 28.
  • 51
    • 0038401493 scopus 로고    scopus 로고
    • note
    • 1.
  • 53
    • 0006639309 scopus 로고
    • Bruker Analytical X-ray Systems: Madison, WI
    • BrukerAXS, SAINT, Integration Software; Bruker Analytical X-ray Systems: Madison, WI, 1995.
    • (1995) BrukerAXS, SAINT, Integration Software
  • 55
    • 0001748025 scopus 로고
    • Spek, A. L. Acta Crystallogr. 1990, A46, C34. Speck, A. L. PLATON, A Multipurpose Crystallographic Tool; Utrecht University: Utrecht, The Netherlands, 2001.
    • (1990) Acta Crystallogr , vol.A46
    • Spek, A.L.1


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