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Volumn 14, Issue 3, 2008, Pages 944-960

Screening of a phosphite-phosphoramidite ligand library for palladium-catalysed asymmetric allylic substitution reactions: The origin of enantioselectivity

Author keywords

Allylic substitution; Asymmetric catalysis; Enantioselectivity; Palladium; pi iigands

Indexed keywords

CATALYSIS; ENANTIOSELECTIVITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PALLADIUM; REACTION RATES; SUBSTITUTION REACTIONS;

EID: 38849087429     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200700852     Document Type: Article
Times cited : (55)

References (40)
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    • A. Pfaltz, M. Lautens in Comprehensive Asymmetric Catalysis, 2 (Eds. : E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, Chapter 24;
    • c) A. Pfaltz, M. Lautens in Comprehensive Asymmetric Catalysis, Vol. 2 (Eds. : E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, Chapter 24;
  • 10
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    • Diphosphites have recently emerged as suitable Iigands for this process offering high activities, see
    • Diphosphites have recently emerged as suitable Iigands for this process offering high activities, see for instance, ref. [3].
    • , vol.3
    • for instance1    ref2
  • 13
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    • The preliminary results were partly reported in the communication: O. Pàmies, M. Diéguez, C Claver, Adv. Synth. Catal. 2007, 349, 836.
    • The preliminary results were partly reported in the communication: O. Pàmies, M. Diéguez, C Claver, Adv. Synth. Catal. 2007, 349, 836.
  • 14
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    • To the best of our knowledge there have been only two successful applications of phosphite-phosphoramidite Iigands in asymmetric catalysis, see: a) ref, 5b, b M. Diéguez, A. Ruiz. C. Claver, Chem. Commun. 2001, 2702
    • To the best of our knowledge there have been only two successful applications of phosphite-phosphoramidite Iigands in asymmetric catalysis, see: a) ref. [5b]; b) M. Diéguez, A. Ruiz. C. Claver, Chem. Commun. 2001, 2702.
  • 16
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    • Similar behaviour was observed by using diphosphite and phosphine-phosphoramidite Iigands, see, for example: a M. Diéguez. A. Ruiz, C. Claver, Dalton Trans. 2003, 2957;
    • Similar behaviour was observed by using diphosphite and phosphine-phosphoramidite Iigands, see, for example: a) M. Diéguez. A. Ruiz, C. Claver, Dalton Trans. 2003, 2957;
  • 21
    • 38849123115 scopus 로고    scopus 로고
    • For some successful applications, sec: a P. Dierkes, S. Randechul, L. Barloy, A. De Cian. J. Fischer. P. C. J. Kamer. P. W. N. M. van Leeuwen, J. A. Osborn, Angew. Chem. 1998, 110, 3299; Angew. Chem. Int. Ed. 1998, 37, 3116;
    • For some successful applications, sec: a) P. Dierkes, S. Randechul, L. Barloy, A. De Cian. J. Fischer. P. C. J. Kamer. P. W. N. M. van Leeuwen, J. A. Osborn, Angew. Chem. 1998, 110, 3299; Angew. Chem. Int. Ed. 1998, 37, 3116;
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    • For some successful applications, see: a
    • For some successful applications, see: a) B. M. Trost, R. C. Bunt, J. Am. Chem. Soc. 1994, 116, 4089;
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    • Trost, B.M.1    Bunt, R.C.2
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    • In contrast to the palladium catalytic systems, the iridium, ruthenium and molybdenum catalysts provide very high selectivity for attack on the non-terminal carbon atom to give the chiral product. See, for instance: a C. Bruneau, J. L. Renaud, B. Demersemen, Chem. Eur. J. 2006, 12, 5178;
    • In contrast to the palladium catalytic systems, the iridium, ruthenium and molybdenum catalysts provide very high selectivity for attack on the non-terminal carbon atom to give the chiral product. See, for instance: a) C. Bruneau, J. L. Renaud, B. Demersemen, Chem. Eur. J. 2006, 12, 5178;
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    • For recent successful applications of palladium catalysts, see: a
    • For recent successful applications of palladium catalysts, see: a) S.-L. You, X.-Z. Zhu, Y-M. Luo, X.-L. Hou, L.-X. Dai, J. Am. Chem. Soc. 2001, 123, 7471;
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    • You, S.-L.1    Zhu, X.-Z.2    Luo, Y.-M.3    Hou, X.-L.4    Dai, L.-X.5
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    • This is in agreement with the fact that the exchange rate constant between isomers A and B is faster than the catalytic rate constants of isomers A and B
    • This is in agreement with the fact that the exchange rate constant between isomers A and B is faster than the catalytic rate constants of isomers A and B.


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