Ligand effects in the hydrogenation of methacycline to doxycycline and epi-doxycycline catalysed by rhodium complexes. Molecular structure of the key catalyst [closo-3,3-(η2,3-C7H7CH2)-3,1,2-Rh C2B9H11]
Felekidis, Apostolos; Goblet-Stachow, M.; Liégeois, Jean-Françoiset al.
1997 • In Journal of Organometallic Chemistry, 536-537, p. 405-412
Ligand effects in the hydrogenation of methacycline to doxycycline and epi-doxycycline catalysed by rhodium complexes. Molecular structure of the key catalyst [closo-3,3-(η2,3-C7H7CH2)-3,1,2-Rh C2B9H11]
[1] H. Brunner, in W.R. Moser and D.W. Slocum (eds.), Advances in Chemistry Series, Homogeneous Transition Metal Catalyzed Reactions, Vol. 230, American Chemical Society, Washington, DC, 1992, p. 143. J.M. Brown, Chem. Soc. Rev., 22 (1993) 25. R.A. Sheldon, Chirotechnology: Industrial Synthesis of Optically Active Compounds, Marcel Dekker, New York, 1993.
[1] H. Brunner, in W.R. Moser and D.W. Slocum (eds.), Advances in Chemistry Series, Homogeneous Transition Metal Catalyzed Reactions, Vol. 230, American Chemical Society, Washington, DC, 1992, p. 143. J.M. Brown, Chem. Soc. Rev., 22 (1993) 25. R.A. Sheldon, Chirotechnology: Industrial Synthesis of Optically Active Compounds, Marcel Dekker, New York, 1993.
[1] H. Brunner, in W.R. Moser and D.W. Slocum (eds.), Advances in Chemistry Series, Homogeneous Transition Metal Catalyzed Reactions, Vol. 230, American Chemical Society, Washington, DC, 1992, p. 143. J.M. Brown, Chem. Soc. Rev., 22 (1993) 25. R.A. Sheldon, Chirotechnology: Industrial Synthesis of Optically Active Compounds, Marcel Dekker, New York, 1993.
[2] D. Arntz and A. Schäfer, in A.F. Noels, M. Graziani and A.J. Hubert (eds.), Catalysis by Metal Complexes, Metal Promoted Selectivity in Organic Synthesis, Vol. 12, Kluwer, 1991, p. 161. H. Takaya, T. Ohta and K. Mashima, in W.R. Moser and D.W. Slocum (eds.), Advances in Chemistry Series, Homogeneous Transition Metal Catalyzed Reactions, Vol. 230, American Chemical Society, Washington, DC, 1992, p. 123. F.P. Pruchnik, in B. Marciniec and J.J. Ziólkowski (eds.), Education in Advanced Chemistry, Principles and Advances in Molecular Catalysis, Vol. 1, Wydawnictwo Uniwersytetu Wroclawskiego, Poznan-Wroclaw, Dordrecht, 1993, p. 79.
[2] D. Arntz and A. Schäfer, in A.F. Noels, M. Graziani and A.J. Hubert (eds.), Catalysis by Metal Complexes, Metal Promoted Selectivity in Organic Synthesis, Vol. 12, Kluwer, 1991, p. 161. H. Takaya, T. Ohta and K. Mashima, in W.R. Moser and D.W. Slocum (eds.), Advances in Chemistry Series, Homogeneous Transition Metal Catalyzed Reactions, Vol. 230, American Chemical Society, Washington, DC, 1992, p. 123. F.P. Pruchnik, in B. Marciniec and J.J. Ziólkowski (eds.), Education in Advanced Chemistry, Principles and Advances in Molecular Catalysis, Vol. 1, Wydawnictwo Uniwersytetu Wroclawskiego, Poznan-Wroclaw, Dordrecht, 1993, p. 79.
[2] D. Arntz and A. Schäfer, in A.F. Noels, M. Graziani and A.J. Hubert (eds.), Catalysis by Metal Complexes, Metal Promoted Selectivity in Organic Synthesis, Vol. 12, Kluwer, 1991, p. 161. H. Takaya, T. Ohta and K. Mashima, in W.R. Moser and D.W. Slocum (eds.), Advances in Chemistry Series, Homogeneous Transition Metal Catalyzed Reactions, Vol. 230, American Chemical Society, Washington, DC, 1992, p. 123. F.P. Pruchnik, in B. Marciniec and J.J. Ziólkowski (eds.), Education in Advanced Chemistry, Principles and Advances in Molecular Catalysis, Vol. 1, Wydawnictwo Uniwersytetu Wroclawskiego, Poznan-Wroclaw, Dordrecht, 1993, p. 79.
[4] B. Pirotte, A. Felekidis, M. Fontaine, A. Demonceau, A.F. Noels, J. Delarge, I.T. Chizhevsky, T.V. Zinevich, I.V. Pisareva and V.I. Bregadze, Tetrahedron Lett., 34 (1993) 1471.
[5] M.E. Wolff (ed.), Burger's Medicinal Chemistry, Vol. 2, Nonlactam Antibiotics, 4th edn., 1979, p. 226. A. Korolkovas, Essentials of Medicinal Chemistry, Chemothempeutic Agents - Anti-infective Agents, Wiley Interscience, 2nd edn., 1988, p. 797.
[5] M.E. Wolff (ed.), Burger's Medicinal Chemistry, Vol. 2, Nonlactam Antibiotics, 4th edn., 1979, p. 226. A. Korolkovas, Essentials of Medicinal Chemistry, Chemothempeutic Agents -Anti-infective Agents, Wiley Interscience, 2nd edn., 1988, p. 797.
[6] A. Felekidis, M. Goblet-Stachow, J.F. Liégeois, B. Pirotte, J. Delarge, A. Demonceau, M. Fontaine, A.F. Noels, I.T. Chizhevsky, T.V. Zinevich and V.I. Bregadze, J. Pharm. Belg., 50 (1995) 232.
[7] R. Broggi and G. Cotti (Ankerfarm S.p.A.), German Patent 2308227, August 30, 1973, Chem. Abstr., 79 (1973) 136908r. T.M. Brennan and H. Faubl (Pfizer Inc.), German Patent 2403714, August 22, 1974, Chem. Abstr., 82 (1975) 43099z. G. Cotti (Ankerfarm S.p.A.), German Patent 2446587, April 3, 1975, Chem. Abstr., 83 (1975) 114090y.
[7] R. Broggi and G. Cotti (Ankerfarm S.p.A.), German Patent 2308227, August 30, 1973, Chem. Abstr., 79 (1973) 136908r. T.M. Brennan and H. Faubl (Pfizer Inc.), German Patent 2403714, August 22, 1974, Chem. Abstr., 82 (1975) 43099z. G. Cotti (Ankerfarm S.p.A.), German Patent 2446587, April 3, 1975, Chem. Abstr., 83 (1975) 114090y.
[7] R. Broggi and G. Cotti (Ankerfarm S.p.A.), German Patent 2308227, August 30, 1973, Chem. Abstr., 79 (1973) 136908r. T.M. Brennan and H. Faubl (Pfizer Inc.), German Patent 2403714, August 22, 1974, Chem. Abstr., 82 (1975) 43099z. G. Cotti (Ankerfarm S.p.A.), German Patent 2446587, April 3, 1975, Chem. Abstr., 83 (1975) 114090y.
[8] P.R. Page and I. Villax (Plurichemie Anstalt), US Patent 4743699, May 10, 1988, Chem. Abstr., 110 (1989) 2142494d. W. Heggie, M.B. Hursthouse, P.R. Page, R.G. Somerville, and I. Villax (Plurichemie Anstalt), European Patent Appl. EP 283615, September 28, 1988, Chem. Abstr., 110 (1989) 78059k. W. Heggie, P.R. Page, I. Villax, I. Ghatak and M.B. Hursthouse (Plurichemie Anstalt), European Patent Appl. EP 283616, September 28, 1988, Chem. Abstr., 110 (1989) 64523v.
[8] P.R. Page and I. Villax (Plurichemie Anstalt), US Patent 4743699, May 10, 1988, Chem. Abstr., 110 (1989) 2142494d. W. Heggie, M.B. Hursthouse, P.R. Page, R.G. Somerville, and I. Villax (Plurichemie Anstalt), European Patent Appl. EP 283615, September 28, 1988, Chem. Abstr., 110 (1989) 78059k. W. Heggie, P.R. Page, I. Villax, I. Ghatak and M.B. Hursthouse (Plurichemie Anstalt), European Patent Appl. EP 283616, September 28, 1988, Chem. Abstr., 110 (1989) 64523v.
[8] P.R. Page and I. Villax (Plurichemie Anstalt), US Patent 4743699, May 10, 1988, Chem. Abstr., 110 (1989) 2142494d. W. Heggie, M.B. Hursthouse, P.R. Page, R.G. Somerville, and I. Villax (Plurichemie Anstalt), European Patent Appl. EP 283615, September 28, 1988, Chem. Abstr., 110 (1989) 78059k. W. Heggie, P.R. Page, I. Villax, I. Ghatak and M.B. Hursthouse (Plurichemie Anstalt), European Patent Appl. EP 283616, September 28, 1988, Chem. Abstr., 110 (1989) 64523v.
[9] M.F. Hawthorne, D.C. Young and P.A. Wagner, J. Am. Chem. Soc., 87 (1965) 1818.
[14] W. Heggie, in J. Pedrosa de Jesus (ed.), Catalysis, Activation and Selectivity Promoted by Metals in Organic Synthesis, Industrial Applications of Hydrogenations in Complex Molecules, Aveiro, Portugal, July 14-21, 1992, p. 177.