Enantiomerically pure palladacycles with one stereogenic Csp3 center directly bonded to the metal

Tetrahedron Asymmetry

Volumn 7, Issue 1, 1996, Pages 139-148

  García Ruano, José L ^a   González, Ana M ^a   Bárcena, Ana I ^a   Camazón, María J ^a   Navarro Ranninger, Carmen ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM COMPLEX;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; X RAY DIFFRACTION;

EID: 0343897924     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(95)00430-0     Document Type: Article

References (31)

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4. Lippard, S.J. Platinum and other Metal Chemotherapeutic Agents (ACS Symp. Ser. 1983, 209), Melanson, R.; Chevrotiere, C.; Rochon, F. Acta Crystallogr., Sect C, 1985, 41, 1428. Kagan, H.B.; Ronan, B. Rev. Heteroatom Chem., Vol. 7, 1992, 92, and references cited therein.
5. Lippard, S.J. Platinum and other Metal Chemotherapeutic Agents (ACS Symp. Ser. 1983, 209), Melanson, R.; Chevrotiere, C.; Rochon, F. Acta Crystallogr., Sect C, 1985, 41, 1428. Kagan, H.B.; Ronan, B. Rev. Heteroatom Chem., Vol. 7, 1992, 92, and references cited therein.
6. The coordination through the oxygen was initially restricted to those cases with a large steric hindrance (Annibale, G.; Cattalini, L.; Bertolasi, V.; Ferretti, V.; Gilli, G.; Tobe. M.L. J. Chem. Soc., Dalton Trans. 1989, 1265.) but later extended to those others with a strong trans effect of the substituents σ-bonded to the metal (Alvarez-Valdés. A.; García-Ruano, J.L.; López-Solera, I.; Masaguer, J.R.; Navarro-Ranninger, C.; Rodriguez, J.H. Organometallics, 1993, 12, 4104.)
7. The coordination through the oxygen was initially restricted to those cases with a large steric hindrance (Annibale, G.; Cattalini, L.; Bertolasi, V.; Ferretti, V.; Gilli, G.; Tobe. M.L. J. Chem. Soc., Dalton Trans. 1989, 1265.) but later extended to those others with a strong trans effect of the substituents σ-bonded to the metal (Alvarez-Valdés. A.; García-Ruano, J.L.; López-Solera, I.; Masaguer, J.R.; Navarro-Ranninger, C.; Rodriguez, J.H. Organometallics, 1993, 12, 4104.)
8. Ruger, R.; Rittner, W.; Jones, P.; Isenberg, W.; Sheldrick, G.M. Angew Chem., 1981, 93, 389.
9. Stille, J.K.; Hill, D.H., Schneider, P.; Tanaka, M.; Morrison, D.L.; Hegedus, L.S. Organometallics, 1991, 10, 1993. Roth, G.; Sapino, C. Tetrahedron Lett., 1991, 32, 4073. Roth, G.; Fuller, C.E. J. Org. Chem., 1991, 56, 3493.
10. Stille, J.K.; Hill, D.H., Schneider, P.; Tanaka, M.; Morrison, D.L.; Hegedus, L.S. Organometallics, 1991, 10, 1993. Roth, G.; Sapino, C. Tetrahedron Lett., 1991, 32, 4073. Roth, G.; Fuller, C.E. J. Org. Chem., 1991, 56, 3493.
11. Stille, J.K.; Hill, D.H., Schneider, P.; Tanaka, M.; Morrison, D.L.; Hegedus, L.S. Organometallics, 1991, 10, 1993. Roth, G.; Sapino, C. Tetrahedron Lett., 1991, 32, 4073. Roth, G.; Fuller, C.E. J. Org. Chem., 1991, 56, 3493.
12. García-Ruano, J.L.; López-Solera, I.; Masaguer, J.R.; Navarro-Ranninger, C.; Rodríguez, J.H. Organometallics, 1992, 11, 3013.
13. Alvarez-Valdés, A.; García-Ruano, J.L.; López-Solera, I.; Masaguer, J.R.; Navarro-Ranninger, C.; Rodríguez, J.H. Organometallics, 1993, 12, 4104.
14. García-Ruano, J.L.; Martín, A.M.; Rodríguez, J.H. J. Org. Chem., 1994, 59, 533. Alonso, I.; Carretero, J.C.; García-Ruano, J.L. ibid 1994, 59, 1499. Arce, E.; Carreño, M.C.; Cid, B., García-Ruano, J.L. ibid, 1994, 59, 3421.
15. García-Ruano, J.L.; Martín, A.M.; Rodríguez, J.H. J. Org. Chem., 1994, 59, 533. Alonso, I.; Carretero, J.C.; García-Ruano, J.L. ibid 1994, 59, 1499. Arce, E.; Carreño, M.C.; Cid, B., García-Ruano, J.L. ibid, 1994, 59, 3421.
16. García-Ruano, J.L.; Martín, A.M.; Rodríguez, J.H. J. Org. Chem., 1994, 59, 533. Alonso, I.; Carretero, J.C.; García-Ruano, J.L. ibid 1994, 59, 1499. Arce, E.; Carreño, M.C.; Cid, B., García-Ruano, J.L. ibid, 1994, 59, 3421.
17. 2SO, which afforded a complex which contain puckered four-membered ring with two C-Pt bonds (Henderson, W.; Kemmitt, R.D.W.; Fawcett, J.; Prouse, L.J.S.; Russell, D.R. J. Chem. Soc., Chem. Commun., 1986, 1791. Henderson, W.; Kemmitt, R.D.W.; Prouse, L.J.S.; Russell, D.R. J. Chem. Soc., Dalton Trans., 1990, 1853). Similar insertion reactions have been observed starting from β-ketoesters (Clarke, D.A.; Kemmitt, R.D.W.; Mazid, M.A.; Mckenna, P.; Russell, D.R.; Schilling, M.D.; Sherry, L.J.S. J. Chem. Soc., Dalton Trans. 1984, 1993) and β-ketosulfones (Henderson, W.; Kemmitt, R.D.W.; Prouse, L.J.S.; Russell, D.R. J. Chem. Soc., Dalton Trans., 1989, 259). With some of these ligands (but no for sulfoxides) palladium complexes have also been also obtained.
18. 2SO, which afforded a complex which contain puckered four-membered ring with two C-Pt bonds (Henderson, W.; Kemmitt, R.D.W.; Fawcett, J.; Prouse, L.J.S.; Russell, D.R. J. Chem. Soc., Chem. Commun., 1986, 1791. Henderson, W.; Kemmitt, R.D.W.; Prouse, L.J.S.; Russell, D.R. J. Chem. Soc., Dalton Trans., 1990, 1853). Similar insertion reactions have been observed starting from β-ketoesters (Clarke, D.A.; Kemmitt, R.D.W.; Mazid, M.A.; Mckenna, P.; Russell, D.R.; Schilling, M.D.; Sherry, L.J.S. J. Chem. Soc., Dalton Trans. 1984, 1993) and β-ketosulfones (Henderson, W.; Kemmitt, R.D.W.; Prouse, L.J.S.; Russell, D.R. J. Chem. Soc., Dalton Trans., 1989, 259). With some of these ligands (but no for sulfoxides) palladium complexes have also been also obtained.
19. 2SO, which afforded a complex which contain puckered four-membered ring with two C-Pt bonds (Henderson, W.; Kemmitt, R.D.W.; Fawcett, J.; Prouse, L.J.S.; Russell, D.R. J. Chem. Soc., Chem. Commun., 1986, 1791. Henderson, W.; Kemmitt, R.D.W.; Prouse, L.J.S.; Russell, D.R. J. Chem. Soc., Dalton Trans., 1990, 1853). Similar insertion reactions have been observed starting from β-ketoesters (Clarke, D.A.; Kemmitt, R.D.W.; Mazid, M.A.; Mckenna, P.; Russell, D.R.; Schilling, M.D.; Sherry, L.J.S. J. Chem. Soc., Dalton Trans. 1984, 1993) and β-ketosulfones (Henderson, W.; Kemmitt, R.D.W.; Prouse, L.J.S.; Russell, D.R. J. Chem. Soc., Dalton Trans., 1989, 259). With some of these ligands (but no for sulfoxides) palladium complexes have also been also obtained.
20. 2SO, which afforded a complex which contain puckered four-membered ring with two C-Pt bonds (Henderson, W.; Kemmitt, R.D.W.; Fawcett, J.; Prouse, L.J.S.; Russell, D.R. J. Chem. Soc., Chem. Commun., 1986, 1791. Henderson, W.; Kemmitt, R.D.W.; Prouse, L.J.S.; Russell, D.R. J. Chem. Soc., Dalton Trans., 1990, 1853). Similar insertion reactions have been observed starting from β-ketoesters (Clarke, D.A.; Kemmitt, R.D.W.; Mazid, M.A.; Mckenna, P.; Russell, D.R.; Schilling, M.D.; Sherry, L.J.S. J. Chem. Soc., Dalton Trans. 1984, 1993) and β-ketosulfones (Henderson, W.; Kemmitt, R.D.W.; Prouse, L.J.S.; Russell, D.R. J. Chem. Soc., Dalton Trans., 1989, 259). With some of these ligands (but no for sulfoxides) palladium complexes have also been also obtained.
21. García-Ruano, J.L.; González, A.M.; López-Solera, I.; Masaguer, J.R.; Navarro-Ranninger, C.; Raithby, P.R.; Rodríguez, J.H. Angew. Chem. Int. Ed. Engl., 1995, 34(12), 1351.
22. Nakamoto K. IR and Raman spectra of Inorganic and Coordination Compounds, 3rd Ed.; Wiley-Interscience, New York, 1978; p. 232.
23. Fawcett, J.; Henderson, W.; Kemmitt, R.D.W.; Prouse, L.J.S.; Russell, D.R. J. Chem. Soc., Dalton Trans., 1991, 2595.
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25. Davies J.A. Adv. Inorg. Chem. Radiochem., 1981, 24, 115. James B.R.; Morris H.R. Can. J. Chem., 1980, 58, 399.
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31. Annunziata, R.; Cinquini, M.; Lozzi, F. J. Chem. Soc., Perkin Trans. I, 1979, 1687.