Molecular mechanics predictions and experimental testing of asymmetric palladium-catalyzed allylation reactions using new chiral phenanthroline ligands

Journal of the American Chemical Society

Volumn 118, Issue 18, 1996, Pages 4299-4313

  Peña Cabrera, Eduarde ^a   Norrby, Per Ola ^b   Sjögren, Magnus ^c   Vitagliano, Aldo ^d   De Felice, Vineenzo ^e   Oslob, Johan ^c   Ishii, Sbingo ^a   O'Neill, David ^a   Åkermark, Björn ^c   Helquist, Paul ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

^c ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

^d UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^e UNIVERSITY OF MOLISE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM COMPLEX; PHENANTHROLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; MECHANICS; MOLECULAR DYNAMICS; PREDICTION;

EID: 0343136162     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja950860t     Document Type: Article

References (61)

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5. (e) Università del Molise.
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15. For general reviews of molecular mechanics, see: (a) Burkert, U.; Allinger, N. L. Molecular Mechanics; American Chemical Society: Washington, 1982. (b) Brubaker, G. R.; Johnson, D. W. Coord. Chem. Rev. 1984, 53, 1. (c) Hancock, R. D. Prog. Inorg. Chem. 1989, 37, 187.
16. For general reviews of molecular mechanics, see: (a) Burkert, U.; Allinger, N. L. Molecular Mechanics; American Chemical Society: Washington, 1982. (b) Brubaker, G. R.; Johnson, D. W. Coord. Chem. Rev. 1984, 53, 1. (c) Hancock, R. D. Prog. Inorg. Chem. 1989, 37, 187.
17. For some representative examples of molecular mechanics calculations on metalcontaining systems, see: (d) Laier, T.; Larsen, E. Acta Chem. Scand. A 1979, 33, 257. (e) Lauher, J. W. J. Am. Chem. Soc. 1986, 108, 1521. (f) Brown, J. M.; Evans, P. L.; Lucy, A. R. J. Chem. Soc., Perkin Trans. II 1987, 1589. (g) Brown, J. M.: Evans, P. L. Tetrahedron 1988, 44, 4905. (h) Bogdan, P. L.: Irwin, J. J.; Bosnien, B. Organometallics 1989, 8, 1450. (i) Vedani, A.; Huhta, D. W. J. Am. Chem. Soc. 1990, 112, 4759. (J) Lin, Z.; Marks, T. J. J. Am. Chem. Soc. 1990, 112, 5515. (k) Mayo, S. L.; Olafson, B. D.; Goddard, W. A., III J. Phys. Chem. 1990, 94, 8897. (l) Ely, R. S.; Raja, M. Organometallics 1990, 9, 1500. (m) Allured, V. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1991, 113, 1. (n) Adam, K. R.; Antolovich, M.; Brigden, L. G.; Lindoy, L. F. J. Am. Chem. Soc. 1991, 113, 3346. (o) Lee, K. J.; Brown, T. L. Inorg. Chem. 1992, 31, 289. (p) Bernhardt, P. V.; Comba, P. Inorg. Chem. 1992, 31, 2638. (q) Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024. (r) Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3112. (s) Polowin, J.: Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3724. (t) Giovaaneni, J. S.; Kelly, C. M.; Laadis, C. R. J. Am. Chem. Soc. 1993, 115, 4040.
18. For some representative examples of molecular mechanics calculations on metalcontaining systems, see: (d) Laier, T.; Larsen, E. Acta Chem. Scand. A 1979, 33, 257. (e) Lauher, J. W. J. Am. Chem. Soc. 1986, 108, 1521. (f) Brown, J. M.; Evans, P. L.; Lucy, A. R. J. Chem. Soc., Perkin Trans. II 1987, 1589. (g) Brown, J. M.: Evans, P. L. Tetrahedron 1988, 44, 4905. (h) Bogdan, P. L.: Irwin, J. J.; Bosnien, B. Organometallics 1989, 8, 1450. (i) Vedani, A.; Huhta, D. W. J. Am. Chem. Soc. 1990, 112, 4759. (J) Lin, Z.; Marks, T. J. J. Am. Chem. Soc. 1990, 112, 5515. (k) Mayo, S. L.; Olafson, B. D.; Goddard, W. A., III J. Phys. Chem. 1990, 94, 8897. (l) Ely, R. S.; Raja, M. Organometallics 1990, 9, 1500. (m) Allured, V. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1991, 113, 1. (n) Adam, K. R.; Antolovich, M.; Brigden, L. G.; Lindoy, L. F. J. Am. Chem. Soc. 1991, 113, 3346. (o) Lee, K. J.; Brown, T. L. Inorg. Chem. 1992, 31, 289. (p) Bernhardt, P. V.; Comba, P. Inorg. Chem. 1992, 31, 2638. (q) Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024. (r) Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3112. (s) Polowin, J.: Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3724. (t) Giovaaneni, J. S.; Kelly, C. M.; Laadis, C. R. J. Am. Chem. Soc. 1993, 115, 4040.
19. For some representative examples of molecular mechanics calculations on metalcontaining systems, see: (d) Laier, T.; Larsen, E. Acta Chem. Scand. A 1979, 33, 257. (e) Lauher, J. W. J. Am. Chem. Soc. 1986, 108, 1521. (f) Brown, J. M.; Evans, P. L.; Lucy, A. R. J. Chem. Soc., Perkin Trans. II 1987, 1589. (g) Brown, J. M.: Evans, P. L. Tetrahedron 1988, 44, 4905. (h) Bogdan, P. L.: Irwin, J. J.; Bosnien, B. Organometallics 1989, 8, 1450. (i) Vedani, A.; Huhta, D. W. J. Am. Chem. Soc. 1990, 112, 4759. (J) Lin, Z.; Marks, T. J. J. Am. Chem. Soc. 1990, 112, 5515. (k) Mayo, S. L.; Olafson, B. D.; Goddard, W. A., III J. Phys. Chem. 1990, 94, 8897. (l) Ely, R. S.; Raja, M. Organometallics 1990, 9, 1500. (m) Allured, V. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1991, 113, 1. (n) Adam, K. R.; Antolovich, M.; Brigden, L. G.; Lindoy, L. F. J. Am. Chem. Soc. 1991, 113, 3346. (o) Lee, K. J.; Brown, T. L. Inorg. Chem. 1992, 31, 289. (p) Bernhardt, P. V.; Comba, P. Inorg. Chem. 1992, 31, 2638. (q) Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024. (r) Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3112. (s) Polowin, J.: Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3724. (t) Giovaaneni, J. S.; Kelly, C. M.; Laadis, C. R. J. Am. Chem. Soc. 1993, 115, 4040.
20. For some representative examples of molecular mechanics calculations on metalcontaining systems, see: (d) Laier, T.; Larsen, E. Acta Chem. Scand. A 1979, 33, 257. (e) Lauher, J. W. J. Am. Chem. Soc. 1986, 108, 1521. (f) Brown, J. M.; Evans, P. L.; Lucy, A. R. J. Chem. Soc., Perkin Trans. II 1987, 1589. (g) Brown, J. M.: Evans, P. L. Tetrahedron 1988, 44, 4905. (h) Bogdan, P. L.: Irwin, J. J.; Bosnien, B. Organometallics 1989, 8, 1450. (i) Vedani, A.; Huhta, D. W. J. Am. Chem. Soc. 1990, 112, 4759. (J) Lin, Z.; Marks, T. J. J. Am. Chem. Soc. 1990, 112, 5515. (k) Mayo, S. L.; Olafson, B. D.; Goddard, W. A., III J. Phys. Chem. 1990, 94, 8897. (l) Ely, R. S.; Raja, M. Organometallics 1990, 9, 1500. (m) Allured, V. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1991, 113, 1. (n) Adam, K. R.; Antolovich, M.; Brigden, L. G.; Lindoy, L. F. J. Am. Chem. Soc. 1991, 113, 3346. (o) Lee, K. J.; Brown, T. L. Inorg. Chem. 1992, 31, 289. (p) Bernhardt, P. V.; Comba, P. Inorg. Chem. 1992, 31, 2638. (q) Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024. (r) Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3112. (s) Polowin, J.: Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3724. (t) Giovaaneni, J. S.; Kelly, C. M.; Laadis, C. R. J. Am. Chem. Soc. 1993, 115, 4040.
21. For some representative examples of molecular mechanics calculations on metalcontaining systems, see: (d) Laier, T.; Larsen, E. Acta Chem. Scand. A 1979, 33, 257. (e) Lauher, J. W. J. Am. Chem. Soc. 1986, 108, 1521. (f) Brown, J. M.; Evans, P. L.; Lucy, A. R. J. Chem. Soc., Perkin Trans. II 1987, 1589. (g) Brown, J. M.: Evans, P. L. Tetrahedron 1988, 44, 4905. (h) Bogdan, P. L.: Irwin, J. J.; Bosnien, B. Organometallics 1989, 8, 1450. (i) Vedani, A.; Huhta, D. W. J. Am. Chem. Soc. 1990, 112, 4759. (J) Lin, Z.; Marks, T. J. J. Am. Chem. Soc. 1990, 112, 5515. (k) Mayo, S. L.; Olafson, B. D.; Goddard, W. A., III J. Phys. Chem. 1990, 94, 8897. (l) Ely, R. S.; Raja, M. Organometallics 1990, 9, 1500. (m) Allured, V. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1991, 113, 1. (n) Adam, K. R.; Antolovich, M.; Brigden, L. G.; Lindoy, L. F. J. Am. Chem. Soc. 1991, 113, 3346. (o) Lee, K. J.; Brown, T. L. Inorg. Chem. 1992, 31, 289. (p) Bernhardt, P. V.; Comba, P. Inorg. Chem. 1992, 31, 2638. (q) Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024. (r) Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3112. (s) Polowin, J.: Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3724. (t) Giovaaneni, J. S.; Kelly, C. M.; Laadis, C. R. J. Am. Chem. Soc. 1993, 115, 4040.
22. For some representative examples of molecular mechanics calculations on metalcontaining systems, see: (d) Laier, T.; Larsen, E. Acta Chem. Scand. A 1979, 33, 257. (e) Lauher, J. W. J. Am. Chem. Soc. 1986, 108, 1521. (f) Brown, J. M.; Evans, P. L.; Lucy, A. R. J. Chem. Soc., Perkin Trans. II 1987, 1589. (g) Brown, J. M.: Evans, P. L. Tetrahedron 1988, 44, 4905. (h) Bogdan, P. L.: Irwin, J. J.; Bosnien, B. Organometallics 1989, 8, 1450. (i) Vedani, A.; Huhta, D. W. J. Am. Chem. Soc. 1990, 112, 4759. (J) Lin, Z.; Marks, T. J. J. Am. Chem. Soc. 1990, 112, 5515. (k) Mayo, S. L.; Olafson, B. D.; Goddard, W. A., III J. Phys. Chem. 1990, 94, 8897. (l) Ely, R. S.; Raja, M. Organometallics 1990, 9, 1500. (m) Allured, V. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1991, 113, 1. (n) Adam, K. R.; Antolovich, M.; Brigden, L. G.; Lindoy, L. F. J. Am. Chem. Soc. 1991, 113, 3346. (o) Lee, K. J.; Brown, T. L. Inorg. Chem. 1992, 31, 289. (p) Bernhardt, P. V.; Comba, P. Inorg. Chem. 1992, 31, 2638. (q) Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024. (r) Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3112. (s) Polowin, J.: Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3724. (t) Giovaaneni, J. S.; Kelly, C. M.; Laadis, C. R. J. Am. Chem. Soc. 1993, 115, 4040.
23. For some representative examples of molecular mechanics calculations on metalcontaining systems, see: (d) Laier, T.; Larsen, E. Acta Chem. Scand. A 1979, 33, 257. (e) Lauher, J. W. J. Am. Chem. Soc. 1986, 108, 1521. (f) Brown, J. M.; Evans, P. L.; Lucy, A. R. J. Chem. Soc., Perkin Trans. II 1987, 1589. (g) Brown, J. M.: Evans, P. L. Tetrahedron 1988, 44, 4905. (h) Bogdan, P. L.: Irwin, J. J.; Bosnien, B. Organometallics 1989, 8, 1450. (i) Vedani, A.; Huhta, D. W. J. Am. Chem. Soc. 1990, 112, 4759. (J) Lin, Z.; Marks, T. J. J. Am. Chem. Soc. 1990, 112, 5515. (k) Mayo, S. L.; Olafson, B. D.; Goddard, W. A., III J. Phys. Chem. 1990, 94, 8897. (l) Ely, R. S.; Raja, M. Organometallics 1990, 9, 1500. (m) Allured, V. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1991, 113, 1. (n) Adam, K. R.; Antolovich, M.; Brigden, L. G.; Lindoy, L. F. J. Am. Chem. Soc. 1991, 113, 3346. (o) Lee, K. J.; Brown, T. L. Inorg. Chem. 1992, 31, 289. (p) Bernhardt, P. V.; Comba, P. Inorg. Chem. 1992, 31, 2638. (q) Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024. (r) Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3112. (s) Polowin, J.: Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3724. (t) Giovaaneni, J. S.; Kelly, C. M.; Laadis, C. R. J. Am. Chem. Soc. 1993, 115, 4040.
24. For some representative examples of molecular mechanics calculations on metalcontaining systems, see: (d) Laier, T.; Larsen, E. Acta Chem. Scand. A 1979, 33, 257. (e) Lauher, J. W. J. Am. Chem. Soc. 1986, 108, 1521. (f) Brown, J. M.; Evans, P. L.; Lucy, A. R. J. Chem. Soc., Perkin Trans. II 1987, 1589. (g) Brown, J. M.: Evans, P. L. Tetrahedron 1988, 44, 4905. (h) Bogdan, P. L.: Irwin, J. J.; Bosnien, B. Organometallics 1989, 8, 1450. (i) Vedani, A.; Huhta, D. W. J. Am. Chem. Soc. 1990, 112, 4759. (J) Lin, Z.; Marks, T. J. J. Am. Chem. Soc. 1990, 112, 5515. (k) Mayo, S. L.; Olafson, B. D.; Goddard, W. A., III J. Phys. Chem. 1990, 94, 8897. (l) Ely, R. S.; Raja, M. Organometallics 1990, 9, 1500. (m) Allured, V. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1991, 113, 1. (n) Adam, K. R.; Antolovich, M.; Brigden, L. G.; Lindoy, L. F. J. Am. Chem. Soc. 1991, 113, 3346. (o) Lee, K. J.; Brown, T. L. Inorg. Chem. 1992, 31, 289. (p) Bernhardt, P. V.; Comba, P. Inorg. Chem. 1992, 31, 2638. (q) Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024. (r) Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3112. (s) Polowin, J.: Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3724. (t) Giovaaneni, J. S.; Kelly, C. M.; Laadis, C. R. J. Am. Chem. Soc. 1993, 115, 4040.
25. For some representative examples of molecular mechanics calculations on metalcontaining systems, see: (d) Laier, T.; Larsen, E. Acta Chem. Scand. A 1979, 33, 257. (e) Lauher, J. W. J. Am. Chem. Soc. 1986, 108, 1521. (f) Brown, J. M.; Evans, P. L.; Lucy, A. R. J. Chem. Soc., Perkin Trans. II 1987, 1589. (g) Brown, J. M.: Evans, P. L. Tetrahedron 1988, 44, 4905. (h) Bogdan, P. L.: Irwin, J. J.; Bosnien, B. Organometallics 1989, 8, 1450. (i) Vedani, A.; Huhta, D. W. J. Am. Chem. Soc. 1990, 112, 4759. (J) Lin, Z.; Marks, T. J. J. Am. Chem. Soc. 1990, 112, 5515. (k) Mayo, S. L.; Olafson, B. D.; Goddard, W. A., III J. Phys. Chem. 1990, 94, 8897. (l) Ely, R. S.; Raja, M. Organometallics 1990, 9, 1500. (m) Allured, V. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1991, 113, 1. (n) Adam, K. R.; Antolovich, M.; Brigden, L. G.; Lindoy, L. F. J. Am. Chem. Soc. 1991, 113, 3346. (o) Lee, K. J.; Brown, T. L. Inorg. Chem. 1992, 31, 289. (p) Bernhardt, P. V.; Comba, P. Inorg. Chem. 1992, 31, 2638. (q) Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024. (r) Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3112. (s) Polowin, J.: Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3724. (t) Giovaaneni, J. S.; Kelly, C. M.; Laadis, C. R. J. Am. Chem. Soc. 1993, 115, 4040.
26. For some representative examples of molecular mechanics calculations on metalcontaining systems, see: (d) Laier, T.; Larsen, E. Acta Chem. Scand. A 1979, 33, 257. (e) Lauher, J. W. J. Am. Chem. Soc. 1986, 108, 1521. (f) Brown, J. M.; Evans, P. L.; Lucy, A. R. J. Chem. Soc., Perkin Trans. II 1987, 1589. (g) Brown, J. M.: Evans, P. L. Tetrahedron 1988, 44, 4905. (h) Bogdan, P. L.: Irwin, J. J.; Bosnien, B. Organometallics 1989, 8, 1450. (i) Vedani, A.; Huhta, D. W. J. Am. Chem. Soc. 1990, 112, 4759. (J) Lin, Z.; Marks, T. J. J. Am. Chem. Soc. 1990, 112, 5515. (k) Mayo, S. L.; Olafson, B. D.; Goddard, W. A., III J. Phys. Chem. 1990, 94, 8897. (l) Ely, R. S.; Raja, M. Organometallics 1990, 9, 1500. (m) Allured, V. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1991, 113, 1. (n) Adam, K. R.; Antolovich, M.; Brigden, L. G.; Lindoy, L. F. J. Am. Chem. Soc. 1991, 113, 3346. (o) Lee, K. J.; Brown, T. L. Inorg. Chem. 1992, 31, 289. (p) Bernhardt, P. V.; Comba, P. Inorg. Chem. 1992, 31, 2638. (q) Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024. (r) Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3112. (s) Polowin, J.: Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3724. (t) Giovaaneni, J. S.; Kelly, C. M.; Laadis, C. R. J. Am. Chem. Soc. 1993, 115, 4040.
27. For some representative examples of molecular mechanics calculations on metalcontaining systems, see: (d) Laier, T.; Larsen, E. Acta Chem. Scand. A 1979, 33, 257. (e) Lauher, J. W. J. Am. Chem. Soc. 1986, 108, 1521. (f) Brown, J. M.; Evans, P. L.; Lucy, A. R. J. Chem. Soc., Perkin Trans. II 1987, 1589. (g) Brown, J. M.: Evans, P. L. Tetrahedron 1988, 44, 4905. (h) Bogdan, P. L.: Irwin, J. J.; Bosnien, B. Organometallics 1989, 8, 1450. (i) Vedani, A.; Huhta, D. W. J. Am. Chem. Soc. 1990, 112, 4759. (J) Lin, Z.; Marks, T. J. J. Am. Chem. Soc. 1990, 112, 5515. (k) Mayo, S. L.; Olafson, B. D.; Goddard, W. A., III J. Phys. Chem. 1990, 94, 8897. (l) Ely, R. S.; Raja, M. Organometallics 1990, 9, 1500. (m) Allured, V. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1991, 113, 1. (n) Adam, K. R.; Antolovich, M.; Brigden, L. G.; Lindoy, L. F. J. Am. Chem. Soc. 1991, 113, 3346. (o) Lee, K. J.; Brown, T. L. Inorg. Chem. 1992, 31, 289. (p) Bernhardt, P. V.; Comba, P. Inorg. Chem. 1992, 31, 2638. (q) Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024. (r) Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3112. (s) Polowin, J.: Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3724. (t) Giovaaneni, J. S.; Kelly, C. M.; Laadis, C. R. J. Am. Chem. Soc. 1993, 115, 4040.
28. For some representative examples of molecular mechanics calculations on metalcontaining systems, see: (d) Laier, T.; Larsen, E. Acta Chem. Scand. A 1979, 33, 257. (e) Lauher, J. W. J. Am. Chem. Soc. 1986, 108, 1521. (f) Brown, J. M.; Evans, P. L.; Lucy, A. R. J. Chem. Soc., Perkin Trans. II 1987, 1589. (g) Brown, J. M.: Evans, P. L. Tetrahedron 1988, 44, 4905. (h) Bogdan, P. L.: Irwin, J. J.; Bosnien, B. Organometallics 1989, 8, 1450. (i) Vedani, A.; Huhta, D. W. J. Am. Chem. Soc. 1990, 112, 4759. (J) Lin, Z.; Marks, T. J. J. Am. Chem. Soc. 1990, 112, 5515. (k) Mayo, S. L.; Olafson, B. D.; Goddard, W. A., III J. Phys. Chem. 1990, 94, 8897. (l) Ely, R. S.; Raja, M. Organometallics 1990, 9, 1500. (m) Allured, V. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1991, 113, 1. (n) Adam, K. R.; Antolovich, M.; Brigden, L. G.; Lindoy, L. F. J. Am. Chem. Soc. 1991, 113, 3346. (o) Lee, K. J.; Brown, T. L. Inorg. Chem. 1992, 31, 289. (p) Bernhardt, P. V.; Comba, P. Inorg. Chem. 1992, 31, 2638. (q) Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024. (r) Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3112. (s) Polowin, J.: Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3724. (t) Giovaaneni, J. S.; Kelly, C. M.; Laadis, C. R. J. Am. Chem. Soc. 1993, 115, 4040.
29. For some representative examples of molecular mechanics calculations on metalcontaining systems, see: (d) Laier, T.; Larsen, E. Acta Chem. Scand. A 1979, 33, 257. (e) Lauher, J. W. J. Am. Chem. Soc. 1986, 108, 1521. (f) Brown, J. M.; Evans, P. L.; Lucy, A. R. J. Chem. Soc., Perkin Trans. II 1987, 1589. (g) Brown, J. M.: Evans, P. L. Tetrahedron 1988, 44, 4905. (h) Bogdan, P. L.: Irwin, J. J.; Bosnien, B. Organometallics 1989, 8, 1450. (i) Vedani, A.; Huhta, D. W. J. Am. Chem. Soc. 1990, 112, 4759. (J) Lin, Z.; Marks, T. J. J. Am. Chem. Soc. 1990, 112, 5515. (k) Mayo, S. L.; Olafson, B. D.; Goddard, W. A., III J. Phys. Chem. 1990, 94, 8897. (l) Ely, R. S.; Raja, M. Organometallics 1990, 9, 1500. (m) Allured, V. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1991, 113, 1. (n) Adam, K. R.; Antolovich, M.; Brigden, L. G.; Lindoy, L. F. J. Am. Chem. Soc. 1991, 113, 3346. (o) Lee, K. J.; Brown, T. L. Inorg. Chem. 1992, 31, 289. (p) Bernhardt, P. V.; Comba, P. Inorg. Chem. 1992, 31, 2638. (q) Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024. (r) Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3112. (s) Polowin, J.: Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3724. (t) Giovaaneni, J. S.; Kelly, C. M.; Laadis, C. R. J. Am. Chem. Soc. 1993, 115, 4040.
30. For some representative examples of molecular mechanics calculations on metalcontaining systems, see: (d) Laier, T.; Larsen, E. Acta Chem. Scand. A 1979, 33, 257. (e) Lauher, J. W. J. Am. Chem. Soc. 1986, 108, 1521. (f) Brown, J. M.; Evans, P. L.; Lucy, A. R. J. Chem. Soc., Perkin Trans. II 1987, 1589. (g) Brown, J. M.: Evans, P. L. Tetrahedron 1988, 44, 4905. (h) Bogdan, P. L.: Irwin, J. J.; Bosnien, B. Organometallics 1989, 8, 1450. (i) Vedani, A.; Huhta, D. W. J. Am. Chem. Soc. 1990, 112, 4759. (J) Lin, Z.; Marks, T. J. J. Am. Chem. Soc. 1990, 112, 5515. (k) Mayo, S. L.; Olafson, B. D.; Goddard, W. A., III J. Phys. Chem. 1990, 94, 8897. (l) Ely, R. S.; Raja, M. Organometallics 1990, 9, 1500. (m) Allured, V. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1991, 113, 1. (n) Adam, K. R.; Antolovich, M.; Brigden, L. G.; Lindoy, L. F. J. Am. Chem. Soc. 1991, 113, 3346. (o) Lee, K. J.; Brown, T. L. Inorg. Chem. 1992, 31, 289. (p) Bernhardt, P. V.; Comba, P. Inorg. Chem. 1992, 31, 2638. (q) Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024. (r) Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3112. (s) Polowin, J.: Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3724. (t) Giovaaneni, J. S.; Kelly, C. M.; Laadis, C. R. J. Am. Chem. Soc. 1993, 115, 4040.
31. For some representative examples of molecular mechanics calculations on metalcontaining systems, see: (d) Laier, T.; Larsen, E. Acta Chem. Scand. A 1979, 33, 257. (e) Lauher, J. W. J. Am. Chem. Soc. 1986, 108, 1521. (f) Brown, J. M.; Evans, P. L.; Lucy, A. R. J. Chem. Soc., Perkin Trans. II 1987, 1589. (g) Brown, J. M.: Evans, P. L. Tetrahedron 1988, 44, 4905. (h) Bogdan, P. L.: Irwin, J. J.; Bosnien, B. Organometallics 1989, 8, 1450. (i) Vedani, A.; Huhta, D. W. J. Am. Chem. Soc. 1990, 112, 4759. (J) Lin, Z.; Marks, T. J. J. Am. Chem. Soc. 1990, 112, 5515. (k) Mayo, S. L.; Olafson, B. D.; Goddard, W. A., III J. Phys. Chem. 1990, 94, 8897. (l) Ely, R. S.; Raja, M. Organometallics 1990, 9, 1500. (m) Allured, V. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1991, 113, 1. (n) Adam, K. R.; Antolovich, M.; Brigden, L. G.; Lindoy, L. F. J. Am. Chem. Soc. 1991, 113, 3346. (o) Lee, K. J.; Brown, T. L. Inorg. Chem. 1992, 31, 289. (p) Bernhardt, P. V.; Comba, P. Inorg. Chem. 1992, 31, 2638. (q) Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024. (r) Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3112. (s) Polowin, J.: Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3724. (t) Giovaaneni, J. S.; Kelly, C. M.; Laadis, C. R. J. Am. Chem. Soc. 1993, 115, 4040.
32. For some representative examples of molecular mechanics calculations on metalcontaining systems, see: (d) Laier, T.; Larsen, E. Acta Chem. Scand. A 1979, 33, 257. (e) Lauher, J. W. J. Am. Chem. Soc. 1986, 108, 1521. (f) Brown, J. M.; Evans, P. L.; Lucy, A. R. J. Chem. Soc., Perkin Trans. II 1987, 1589. (g) Brown, J. M.: Evans, P. L. Tetrahedron 1988, 44, 4905. (h) Bogdan, P. L.: Irwin, J. J.; Bosnien, B. Organometallics 1989, 8, 1450. (i) Vedani, A.; Huhta, D. W. J. Am. Chem. Soc. 1990, 112, 4759. (J) Lin, Z.; Marks, T. J. J. Am. Chem. Soc. 1990, 112, 5515. (k) Mayo, S. L.; Olafson, B. D.; Goddard, W. A., III J. Phys. Chem. 1990, 94, 8897. (l) Ely, R. S.; Raja, M. Organometallics 1990, 9, 1500. (m) Allured, V. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1991, 113, 1. (n) Adam, K. R.; Antolovich, M.; Brigden, L. G.; Lindoy, L. F. J. Am. Chem. Soc. 1991, 113, 3346. (o) Lee, K. J.; Brown, T. L. Inorg. Chem. 1992, 31, 289. (p) Bernhardt, P. V.; Comba, P. Inorg. Chem. 1992, 31, 2638. (q) Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024. (r) Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3112. (s) Polowin, J.: Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3724. (t) Giovaaneni, J. S.; Kelly, C. M.; Laadis, C. R. J. Am. Chem. Soc. 1993, 115, 4040.
33. For some representative examples of molecular mechanics calculations on metalcontaining systems, see: (d) Laier, T.; Larsen, E. Acta Chem. Scand. A 1979, 33, 257. (e) Lauher, J. W. J. Am. Chem. Soc. 1986, 108, 1521. (f) Brown, J. M.; Evans, P. L.; Lucy, A. R. J. Chem. Soc., Perkin Trans. II 1987, 1589. (g) Brown, J. M.: Evans, P. L. Tetrahedron 1988, 44, 4905. (h) Bogdan, P. L.: Irwin, J. J.; Bosnien, B. Organometallics 1989, 8, 1450. (i) Vedani, A.; Huhta, D. W. J. Am. Chem. Soc. 1990, 112, 4759. (J) Lin, Z.; Marks, T. J. J. Am. Chem. Soc. 1990, 112, 5515. (k) Mayo, S. L.; Olafson, B. D.; Goddard, W. A., III J. Phys. Chem. 1990, 94, 8897. (l) Ely, R. S.; Raja, M. Organometallics 1990, 9, 1500. (m) Allured, V. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1991, 113, 1. (n) Adam, K. R.; Antolovich, M.; Brigden, L. G.; Lindoy, L. F. J. Am. Chem. Soc. 1991, 113, 3346. (o) Lee, K. J.; Brown, T. L. Inorg. Chem. 1992, 31, 289. (p) Bernhardt, P. V.; Comba, P. Inorg. Chem. 1992, 31, 2638. (q) Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024. (r) Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3112. (s) Polowin, J.: Mackie, S. C.; Baird, M. C. Organometallics 1992, 11, 3724. (t) Giovaaneni, J. S.; Kelly, C. M.; Laadis, C. R. J. Am. Chem. Soc. 1993, 115, 4040.
34. 3-allylpalladium complexes, see: (u) Pregosin, P. S.; Rüegger, H.; Salzmann, R.; Albinati, A.; Lianza, F.; Kunz, R. W. Organometallics 1994, 13, 83. (v) Gugelchuk, M. M.; Houk, K. N. J. Am. Chem. Soc. 1994, 116, 330. (w) Trost, B. M.; Breit, B.; Organ. M. G. Tetrahedron Lett. 1994, 55, 5817. (x) Barbare, P.; Pregosin, P. S.; Salzmann, R.; Albinati, A.; Kunz, R. W. Organometaliics 1995, 14, 5160. (y) Taber, D. F.: You, K. K.; Rheingold. A. L. J. Am. Chem. Soc. 1996, 118, 547. For another extensive bibliography, see ref 3r.
35. 3-allylpalladium complexes, see: (u) Pregosin, P. S.; Rüegger, H.; Salzmann, R.; Albinati, A.; Lianza, F.; Kunz, R. W. Organometallics 1994, 13, 83. (v) Gugelchuk, M. M.; Houk, K. N. J. Am. Chem. Soc. 1994, 116, 330. (w) Trost, B. M.; Breit, B.; Organ. M. G. Tetrahedron Lett. 1994, 55, 5817. (x) Barbare, P.; Pregosin, P. S.; Salzmann, R.; Albinati, A.; Kunz, R. W. Organometaliics 1995, 14, 5160. (y) Taber, D. F.: You, K. K.; Rheingold. A. L. J. Am. Chem. Soc. 1996, 118, 547. For another extensive bibliography, see ref 3r.
36. 3-allylpalladium complexes, see: (u) Pregosin, P. S.; Rüegger, H.; Salzmann, R.; Albinati, A.; Lianza, F.; Kunz, R. W. Organometallics 1994, 13, 83. (v) Gugelchuk, M. M.; Houk, K. N. J. Am. Chem. Soc. 1994, 116, 330. (w) Trost, B. M.; Breit, B.; Organ. M. G. Tetrahedron Lett. 1994, 55, 5817. (x) Barbare, P.; Pregosin, P. S.; Salzmann, R.; Albinati, A.; Kunz, R. W. Organometaliics 1995, 14, 5160. (y) Taber, D. F.: You, K. K.; Rheingold. A. L. J. Am. Chem. Soc. 1996, 118, 547. For another extensive bibliography, see ref 3r.
37. 3-allylpalladium complexes, see: (u) Pregosin, P. S.; Rüegger, H.; Salzmann, R.; Albinati, A.; Lianza, F.; Kunz, R. W. Organometallics 1994, 13, 83. (v) Gugelchuk, M. M.; Houk, K. N. J. Am. Chem. Soc. 1994, 116, 330. (w) Trost, B. M.; Breit, B.; Organ. M. G. Tetrahedron Lett. 1994, 55, 5817. (x) Barbare, P.; Pregosin, P. S.; Salzmann, R.; Albinati, A.; Kunz, R. W. Organometaliics 1995, 14, 5160. (y) Taber, D. F.: You, K. K.; Rheingold. A. L. J. Am. Chem. Soc. 1996, 118, 547. For another extensive bibliography, see ref 3r.
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