Olefin-Amino Acid Complexes of Platinum(II). 2. NMR Study of the Effect of Olefin Structure on the Stability and on the Stereoselectivity of Binding for η2-Coordinated Prochiral Olefins

Inorganic Chemistry

Volumn 36, Issue 3, 1997, Pages 284-290

  Erickson, Luther E ^a   Hayes, Peter ^a   Hooper, Joanna J ^a   Morris, Kevin F ^a   Newbrough, Sally A ^a   Van Os, Marjan ^a   Slangan, Petie ^a  

^a GRINNELL COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0141610052     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic960967x     Document Type: Article

References (36)

1. The stereochemistry of several olefin complexes of Re, in which the asymmetric Re center serves as the chiral template for stereoselective coordination of prochiral olefins (analgous to the platinum complexes reported here), serves as a useful parallel for the work reported here. See: Kowalczyk, J. J.; Arif, A. M.; Glaydz, J. A. Chem. Ber. 1991, 124, 729. Pu, J.; Peng, T.-S.; Mayne, C. L.; Arif, A. M.; Gladyz, J. A. Organometallics 1993, 12, 2686. Pu, J.; Peng, T.-S.; Mayne, A. M.; Gladyz, J. A. Organometallics 1994, 13, 929.
2. The stereochemistry of several olefin complexes of Re, in which the asymmetric Re center serves as the chiral template for stereoselective coordination of prochiral olefins (analgous to the platinum complexes reported here), serves as a useful parallel for the work reported here. See: Kowalczyk, J. J.; Arif, A. M.; Glaydz, J. A. Chem. Ber. 1991, 124, 729. Pu, J.; Peng, T.-S.; Mayne, C. L.; Arif, A. M.; Gladyz, J. A. Organometallics 1993, 12, 2686. Pu, J.; Peng, T.-S.; Mayne, A. M.; Gladyz, J. A. Organometallics 1994, 13, 929.
3. The stereochemistry of several olefin complexes of Re, in which the asymmetric Re center serves as the chiral template for stereoselective coordination of prochiral olefins (analgous to the platinum complexes reported here), serves as a useful parallel for the work reported here. See: Kowalczyk, J. J.; Arif, A. M.; Glaydz, J. A. Chem. Ber. 1991, 124, 729. Pu, J.; Peng, T.-S.; Mayne, C. L.; Arif, A. M.; Gladyz, J. A. Organometallics 1993, 12, 2686. Pu, J.; Peng, T.-S.; Mayne, A. M.; Gladyz, J. A. Organometallics 1994, 13, 929.
4. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
5. Morrison, J. D., Ed., Asymmetric Synthesis, Vol. 1-5; Academic Press: New York, 1983-1985.
6. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley-Interscience: New York, 1994; Chapter 12.
7. Erickson, L. E.; Jones, G. S.; Blanchard, J. L.; Ahmed, K. J. Inorg. Chem. 1991, 30, 3147-3155.
8. Uccello-Barretta, G.; Lazzaroni, R.; Bertucci, C.; Salvadori, P. Organometallics 1987, 6, 550; J. Organomet. Chem. 1985, 297, 117; J. Organomet. Chem. 1984, 275, 145.
9. Uccello-Barretta, G.; Lazzaroni, R.; Bertucci, C.; Salvadori, P. Organometallics 1987, 6, 550; J. Organomet. Chem. 1985, 297, 117; J. Organomet. Chem. 1984, 275, 145.
10. Uccello-Barretta, G.; Lazzaroni, R.; Bertucci, C.; Salvadori, P. Organometallics 1987, 6, 550; J. Organomet. Chem. 1985, 297, 117; J. Organomet. Chem. 1984, 275, 145.
11. Erickson, L. E.; Bemis, J. Fourth International Conference on Bioinorganic Chemistry, MIT, Boston, July 1989. (Abstract in J. Inorg. Biochem. 1989, 36, 256.)
12. Erickson, L. E.; Bemis, J. Fourth International Conference on Bioinorganic Chemistry, MIT, Boston, July 1989. (Abstract in J. Inorg. Biochem. 1989, 36, 256.)
13. Ohrstrom, L. Comments Inorg. Chem. 1996, 18, 305.
14. Morris, K. F.; Erickson, L. E.; Ding, F.; Jiang, D.; Panajotova, B. Inorg. Chem., in press.
15. Erickson, L. E.; Ding, F.; Gross, J.; Morris, K. F.; Panajotova, B., to be submitted for publication.
16. Available through T. Farrar, Department of Chemistry, University of Wisconsin, Madison, WI.
17. Hartley, F. R.; Venanzi, L. M. J. Chem. Soc. A 1967, 330.
18. (a) Freeman, W.; Pregosin, P. S.; Sze, S. J. Magn. Reson. 1976, 22, 473.
19. (b) Pesek, J. J.; Mason, W. R. J. Magn. Reson. 1977, 25, 519.
20. (c) Appleton, T. G.; Hall, J. R.; Ralph, S. F.; Thompson, C. S. M. Inorg. Chem. 1984, 23, 3521.
21. (a) Coley, R. F.; Martin, D. S. Inorg. Chim. Acta 1972, 7, 573.
22. (b) Miller, S. E.; Gerard, J.; House, D. A. Inorg. Chim. Acta 1991, 190, 135.
23. (c) Jestin, J.-L.; Chottard, J. C.; Frey, U.; Laurenczy, G; Merbach, A. E. Inorg. Chem. 1994, 33, 4277.
24. (d) Rochon, F. D.; Morneau, A. Magn. Reson. Chem. 1991, 29, 120.
25. Pimentel, G. C. The Hydrogen Bond; W. H. Freeman and Co.: San Francisco, 1960. Joesten, M. D.; Schaad, L. J. Hydrogen Bonding; Marcel Dekker, Inc: New York, 1974. Zewail, A. Ed., The Chemical Bond Structure and Dynamics; Academic Press, Inc.: New York, 1992.
26. Pimentel, G. C. The Hydrogen Bond; W. H. Freeman and Co.: San Francisco, 1960. Joesten, M. D.; Schaad, L. J. Hydrogen Bonding; Marcel Dekker, Inc: New York, 1974. Zewail, A. Ed., The Chemical Bond Structure and Dynamics; Academic Press, Inc.: New York, 1992.
27. Pimentel, G. C. The Hydrogen Bond; W. H. Freeman and Co.: San Francisco, 1960. Joesten, M. D.; Schaad, L. J. Hydrogen Bonding; Marcel Dekker, Inc: New York, 1974. Zewail, A. Ed., The Chemical Bond Structure and Dynamics; Academic Press, Inc.: New York, 1992.
28. Erickson, L. E.; Hahne, W. F. Inorg. Chem. 1976, 15, 2941.
29. Gessner, R. V.; Quigley, G. J.; Wang, A. H.-J.; van der Marel, G. A.; van Boom, J. H.; Rich, A. Biochemistry 1985, 24, 237.
30. Sarneski, J. E.; Erickson, L. E.; Okarma, P. J.; Sabatelli, A. D.; Cook, D. J.; Evans, G. D. Inorg. Chem. 1990, 29, 1958.
31. Molecular mechanics calculations were carried out with CAChe Molecular Modeling software running on a Macintosh Quadra 700 equipped with the CAChe coprocessor board.
32. Gellman, S. H.; Dado, G. P. Tetrahedron Lett. 1991, 32, 7377.
33. (a) Liang, G.-B.; Desper, J. M.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 925.
34. (b) Dado, G. P.; Gellman, G. H. J. Am. Chem. Soc. 1993, 115, 4228.
35. (c) Gardner, R. R.; Gellman, G. H. J. Am. Chem. Soc. 1995, 117, 10411.
36. Erickson, L. E.; Fritz, H. L.; May, R. J.; Wright, R. J. J. Am. Chem. Soc. 1969, 91, 2513.