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Volumn 9, Issue 18, 2007, Pages 3567-3570

Platinum(II)-coordinated phosphinous acid-catalyzed alkylidenecyclopropanation of bicyclic alkenes with terminal alkynes

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EID: 34548533819     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol071386m     Document Type: Article
Times cited : (70)

References (45)
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    • For recent studies, see
    • (b) For recent studies, see: Polavarapu, P. L.; Wang, F. J. Org. Chem. 2000, 65, 7561-7565.
    • (2000) J. Org. Chem , vol.65 , pp. 7561-7565
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    • For recent reviews, see: a
    • For recent reviews, see: (a) Ackermann, L. Synthesis 2006, 1557-1571.
    • (2006) Synthesis , pp. 1557-1571
    • Ackermann, L.1
  • 25
    • 33846263429 scopus 로고    scopus 로고
    • For recent examples of transition metal catalyzed vinylcyclopropanation of norbornene derivatives, see: a
    • For recent examples of transition metal catalyzed vinylcyclopropanation of norbornene derivatives, see: (a) Trepanier, V. E.; Fillion, E. Organometallics 2007, 26, 30-32.
    • (2007) Organometallics , vol.26 , pp. 30-32
    • Trepanier, V.E.1    Fillion, E.2
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    • and references therein
    • (d) Tenaglia, A.; Marc, S. J. Org. Chem. 2006, 71, 3569-3575 and references therein.
    • (2006) J. Org. Chem , vol.71 , pp. 3569-3575
    • Tenaglia, A.1    Marc, S.2
  • 29
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    • NMR analyses became easier by monitoring the reaction with enantiopure 1. For the enantioselective synthesis of SPOs, see: (a) Leyris, A.; Nuel, D.; Giordano, L.; Achard, M.; Buono, G. Tetrahedron Lett. 2005, 46, 8673-8676.
    • NMR analyses became easier by monitoring the reaction with enantiopure 1. For the enantioselective synthesis of SPOs, see: (a) Leyris, A.; Nuel, D.; Giordano, L.; Achard, M.; Buono, G. Tetrahedron Lett. 2005, 46, 8673-8676.
  • 31
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    • The structures of complexes were deduced from coupling constants between platinum and phosphorus atoms. For the cis isomer, the 1J195Pt-P coupling constant is larger (≈3700 Hz) than that for the trans isomer (≈2500 Hz, For 31P NMR study of tertiary phosphine complexes of platinum(II, see: (a) Grim, S. O, Keiter, R. L, McFarlane, W. Inorg. Chem. 1967, 6, 1133-1137
    • 31P NMR study of tertiary phosphine complexes of platinum(II), see: (a) Grim, S. O.; Keiter, R. L.; McFarlane, W. Inorg. Chem. 1967, 6, 1133-1137.
  • 33
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    • 2 was recently reported: ref 8c.
    • 2 was recently reported: ref 8c.
  • 34
    • 34548523468 scopus 로고    scopus 로고
    • For similar observations, see: -B. Ph.D. Thesis, University of Groningen
    • For similar observations, see: Jiang, X.-B. Ph.D. Thesis, University of Groningen, 2004.
    • (2004)
    • Jiang, X.1
  • 35
    • 34548530030 scopus 로고    scopus 로고
    • The crystallographic data for complex 3a have been deposited with the Cambridge Crystallographic Data Centre (CCDC 644335). These data can be obtained free of charge at www.ccdc.cam.ac.uk/data_request/cif.
    • The crystallographic data for complex 3a have been deposited with the Cambridge Crystallographic Data Centre (CCDC 644335). These data can be obtained free of charge at www.ccdc.cam.ac.uk/data_request/cif.
  • 37
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    • The exo-selectivity for reactions of [2.2.1] bicyclic alkenes is well established. See: Koga, N.; Ozawa, T.; Morokuma, K. J. Phys. Org. Chem. 1990, 3, 519-533.
    • The exo-selectivity for reactions of [2.2.1] bicyclic alkenes is well established. See: Koga, N.; Ozawa, T.; Morokuma, K. J. Phys. Org. Chem. 1990, 3, 519-533.
  • 41
    • 0031046817 scopus 로고    scopus 로고
    • An excess of phenylethyne (5a) leads to a well-known mixture of linear and branched enynes which could be removed by chromatography. Without the presence of alkene, the homocoupling did not proceed. For examples of terminal alkyne-alkyne couplings catalyzed by palladium, see: Trost, B. M, Sorum, M. T, Chan, C, Harms, A. E, Rühter, G. J. Am. Chem. Soc. 1997, 119, 698-708
    • An excess of phenylethyne (5a) leads to a well-known mixture of linear and branched enynes which could be removed by chromatography. Without the presence of alkene, the homocoupling did not proceed. For examples of terminal alkyne-alkyne couplings catalyzed by palladium, see: Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Rühter, G. J. Am. Chem. Soc. 1997, 119, 698-708.
  • 42
    • 34548536619 scopus 로고    scopus 로고
    • The same reaction carried out with cyclopentene in place of strained alkenes did not work
    • The same reaction carried out with cyclopentene in place of strained alkenes did not work.
  • 45
    • 34548543387 scopus 로고    scopus 로고
    • Obtained through our previous Pd-catalyzed alkylidenecyclopropanation: see ref 10
    • Obtained through our previous Pd-catalyzed alkylidenecyclopropanation: see ref 10.


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