Group-4 metallocene cation complexes of oligopeptides: Reaction of [Cp2ZrCH3(THF)+BPh4-] with Boc-protected di- and tripepride esters

European Journal of Inorganic Chemistry

Volumn , Issue 7, 1999, Pages 1111-1120

  Wonnemann, Jörg ^a   Oberhoff, Markus ^a   Erker, Gerhard ^a   Fröhlich, Roland ^a   Bergander, Klaus ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Bioorganometallic chemistry; Group 4 metallocene peptide complexes; Metallocene cations; Zirconocene complexes

Indexed keywords

AMINO ACIDS; CHELATION; CHEMICAL BONDS; COORDINATION REACTIONS; DICHLOROMETHANE; ISOMERS; METHANE; ORGANOMETALLICS; PEPTIDES; TEMPERATURE; X RAY DIFFRACTION; ZIRCONIUM COMPOUNDS;

AMINO ACID RESIDUES; BIO-ORGANOMETALLIC CHEMISTRY; CATION COMPLEX; CHELATE COMPLEX; GROUP 4; GROUP-4 METALLOCENE PEPTIDE COMPLEX; METALLOCENE CATION; N TERMINUS; PEPTIDE COMPLEX; ZIRCONOCENE COMPLEXES;

POSITIVE IONS;

CATION; DIPEPTIDE DERIVATIVE; ESTER; METAL COMPLEX; OLIGOPEPTIDE; TRIPEPTIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMER; REACTION ANALYSIS; STRUCTURE ANALYSIS; THERMODYNAMICS; X RAY DIFFRACTION;

EID: 0032783853     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0682(199907)1999:7<1111::aid-ejic1111>3.0.co;2-a     Document Type: Article

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14. For other representative examples of group-4 metal complexes with amino acid or peptide derivatives see e.g.: C. J. Cardin, A. Roy, Inorg. Chim. Acta 1985, 107, L33. A. Schäfer, E. Karl, E. Zsolnai, G. Huttner, H.-H. Brintzinger, J. Organomet. Chem. 1987, 328, 87. J. Recht, B. I. Cohen, A. S. Goldman, J. Kohn, Tetrahedron Lett. 1990, 31, 7281. T. M. Klapötke, H. Köpf, I. C. Tornipoerth-Oetting, P. S. White, Angew. Chem. 1994, 106, 1587; Angew. Chem. Int. Ed. Engl. 1994, 33, 1518; Organometallics 1994, 13, 3628. I. C. Tornipoerth-Oetting, P. S. White, Organometallics 1995, 14, 1632. K. Severin, W. Beck, G. Trojandt, K. Polborn, W. Steglich, Angew. Chem. 1995, 107, 1570; Angew. Chem. Int. Ed. Engl. 1995, 34, 1449. D. A. Gately, J. R. Norton, J. Am. Chem. Soc. 1996, 118, 3479.
15. For other representative examples of group-4 metal complexes with amino acid or peptide derivatives see e.g.: C. J. Cardin, A. Roy, Inorg. Chim. Acta 1985, 107, L33. A. Schäfer, E. Karl, E. Zsolnai, G. Huttner, H.-H. Brintzinger, J. Organomet. Chem. 1987, 328, 87. J. Recht, B. I. Cohen, A. S. Goldman, J. Kohn, Tetrahedron Lett. 1990, 31, 7281. T. M. Klapötke, H. Köpf, I. C. Tornipoerth-Oetting, P. S. White, Angew. Chem. 1994, 106, 1587; Angew. Chem. Int. Ed. Engl. 1994, 33, 1518; Organometallics 1994, 13, 3628. I. C. Tornipoerth-Oetting, P. S. White, Organometallics 1995, 14, 1632. K. Severin, W. Beck, G. Trojandt, K. Polborn, W. Steglich, Angew. Chem. 1995, 107, 1570; Angew. Chem. Int. Ed. Engl. 1995, 34, 1449. D. A. Gately, J. R. Norton, J. Am. Chem. Soc. 1996, 118, 3479.
16. For other representative examples of group-4 metal complexes with amino acid or peptide derivatives see e.g.: C. J. Cardin, A. Roy, Inorg. Chim. Acta 1985, 107, L33. A. Schäfer, E. Karl, E. Zsolnai, G. Huttner, H.-H. Brintzinger, J. Organomet. Chem. 1987, 328, 87. J. Recht, B. I. Cohen, A. S. Goldman, J. Kohn, Tetrahedron Lett. 1990, 31, 7281. T. M. Klapötke, H. Köpf, I. C. Tornipoerth-Oetting, P. S. White, Angew. Chem. 1994, 106, 1587; Angew. Chem. Int. Ed. Engl. 1994, 33, 1518; Organometallics 1994, 13, 3628. I. C. Tornipoerth-Oetting, P. S. White, Organometallics 1995, 14, 1632. K. Severin, W. Beck, G. Trojandt, K. Polborn, W. Steglich, Angew. Chem. 1995, 107, 1570; Angew. Chem. Int. Ed. Engl. 1995, 34, 1449. D. A. Gately, J. R. Norton, J. Am. Chem. Soc. 1996, 118, 3479.
17. For other representative examples of group-4 metal complexes with amino acid or peptide derivatives see e.g.: C. J. Cardin, A. Roy, Inorg. Chim. Acta 1985, 107, L33. A. Schäfer, E. Karl, E. Zsolnai, G. Huttner, H.-H. Brintzinger, J. Organomet. Chem. 1987, 328, 87. J. Recht, B. I. Cohen, A. S. Goldman, J. Kohn, Tetrahedron Lett. 1990, 31, 7281. T. M. Klapötke, H. Köpf, I. C. Tornipoerth-Oetting, P. S. White, Angew. Chem. 1994, 106, 1587; Angew. Chem. Int. Ed. Engl. 1994, 33, 1518; Organometallics 1994, 13, 3628. I. C. Tornipoerth-Oetting, P. S. White, Organometallics 1995, 14, 1632. K. Severin, W. Beck, G. Trojandt, K. Polborn, W. Steglich, Angew. Chem. 1995, 107, 1570; Angew. Chem. Int. Ed. Engl. 1995, 34, 1449. D. A. Gately, J. R. Norton, J. Am. Chem. Soc. 1996, 118, 3479.
18. For other representative examples of group-4 metal complexes with amino acid or peptide derivatives see e.g.: C. J. Cardin, A. Roy, Inorg. Chim. Acta 1985, 107, L33. A. Schäfer, E. Karl, E. Zsolnai, G. Huttner, H.-H. Brintzinger, J. Organomet. Chem. 1987, 328, 87. J. Recht, B. I. Cohen, A. S. Goldman, J. Kohn, Tetrahedron Lett. 1990, 31, 7281. T. M. Klapötke, H. Köpf, I. C. Tornipoerth-Oetting, P. S. White, Angew. Chem. 1994, 106, 1587; Angew. Chem. Int. Ed. Engl. 1994, 33, 1518; Organometallics 1994, 13, 3628. I. C. Tornipoerth-Oetting, P. S. White, Organometallics 1995, 14, 1632. K. Severin, W. Beck, G. Trojandt, K. Polborn, W. Steglich, Angew. Chem. 1995, 107, 1570; Angew. Chem. Int. Ed. Engl. 1995, 34, 1449. D. A. Gately, J. R. Norton, J. Am. Chem. Soc. 1996, 118, 3479.
19. For other representative examples of group-4 metal complexes with amino acid or peptide derivatives see e.g.: C. J. Cardin, A. Roy, Inorg. Chim. Acta 1985, 107, L33. A. Schäfer, E. Karl, E. Zsolnai, G. Huttner, H.-H. Brintzinger, J. Organomet. Chem. 1987, 328, 87. J. Recht, B. I. Cohen, A. S. Goldman, J. Kohn, Tetrahedron Lett. 1990, 31, 7281. T. M. Klapötke, H. Köpf, I. C. Tornipoerth-Oetting, P. S. White, Angew. Chem. 1994, 106, 1587; Angew. Chem. Int. Ed. Engl. 1994, 33, 1518; Organometallics 1994, 13, 3628. I. C. Tornipoerth-Oetting, P. S. White, Organometallics 1995, 14, 1632. K. Severin, W. Beck, G. Trojandt, K. Polborn, W. Steglich, Angew. Chem. 1995, 107, 1570; Angew. Chem. Int. Ed. Engl. 1995, 34, 1449. D. A. Gately, J. R. Norton, J. Am. Chem. Soc. 1996, 118, 3479.
20. For other representative examples of group-4 metal complexes with amino acid or peptide derivatives see e.g.: C. J. Cardin, A. Roy, Inorg. Chim. Acta 1985, 107, L33. A. Schäfer, E. Karl, E. Zsolnai, G. Huttner, H.-H. Brintzinger, J. Organomet. Chem. 1987, 328, 87. J. Recht, B. I. Cohen, A. S. Goldman, J. Kohn, Tetrahedron Lett. 1990, 31, 7281. T. M. Klapötke, H. Köpf, I. C. Tornipoerth-Oetting, P. S. White, Angew. Chem. 1994, 106, 1587; Angew. Chem. Int. Ed. Engl. 1994, 33, 1518; Organometallics 1994, 13, 3628. I. C. Tornipoerth-Oetting, P. S. White, Organometallics 1995, 14, 1632. K. Severin, W. Beck, G. Trojandt, K. Polborn, W. Steglich, Angew. Chem. 1995, 107, 1570; Angew. Chem. Int. Ed. Engl. 1995, 34, 1449. D. A. Gately, J. R. Norton, J. Am. Chem. Soc. 1996, 118, 3479.
21. For other representative examples of group-4 metal complexes with amino acid or peptide derivatives see e.g.: C. J. Cardin, A. Roy, Inorg. Chim. Acta 1985, 107, L33. A. Schäfer, E. Karl, E. Zsolnai, G. Huttner, H.-H. Brintzinger, J. Organomet. Chem. 1987, 328, 87. J. Recht, B. I. Cohen, A. S. Goldman, J. Kohn, Tetrahedron Lett. 1990, 31, 7281. T. M. Klapötke, H. Köpf, I. C. Tornipoerth-Oetting, P. S. White, Angew. Chem. 1994, 106, 1587; Angew. Chem. Int. Ed. Engl. 1994, 33, 1518; Organometallics 1994, 13, 3628. I. C. Tornipoerth-Oetting, P. S. White, Organometallics 1995, 14, 1632. K. Severin, W. Beck, G. Trojandt, K. Polborn, W. Steglich, Angew. Chem. 1995, 107, 1570; Angew. Chem. Int. Ed. Engl. 1995, 34, 1449. D. A. Gately, J. R. Norton, J. Am. Chem. Soc. 1996, 118, 3479.
22. For other representative examples of group-4 metal complexes with amino acid or peptide derivatives see e.g.: C. J. Cardin, A. Roy, Inorg. Chim. Acta 1985, 107, L33. A. Schäfer, E. Karl, E. Zsolnai, G. Huttner, H.-H. Brintzinger, J. Organomet. Chem. 1987, 328, 87. J. Recht, B. I. Cohen, A. S. Goldman, J. Kohn, Tetrahedron Lett. 1990, 31, 7281. T. M. Klapötke, H. Köpf, I. C. Tornipoerth-Oetting, P. S. White, Angew. Chem. 1994, 106, 1587; Angew. Chem. Int. Ed. Engl. 1994, 33, 1518; Organometallics 1994, 13, 3628. I. C. Tornipoerth-Oetting, P. S. White, Organometallics 1995, 14, 1632. K. Severin, W. Beck, G. Trojandt, K. Polborn, W. Steglich, Angew. Chem. 1995, 107, 1570; Angew. Chem. Int. Ed. Engl. 1995, 34, 1449. D. A. Gately, J. R. Norton, J. Am. Chem. Soc. 1996, 118, 3479.
23. For related methane elimination reactions see e.g.: [6a] A. Bertuleit, C. Fritze, G. Erker, R. Fröhlich, Organometallics 1997, 16, 2891. [6b] J. M. Meyer, C. J. Curtis, J. E. Bercaw, J. Am. Chem. Soc. 1983, 115, 2651. S. E. Buchwald, B. T. Watson, M. W. Wannamaker, C. Dewan, J. Am. Chem. Soc. 1989, 111, 4486. N. Coles, M. C. J. Harris, R. J. Whitby, J. Blagg, Organometallics 1994, 13, 190. [6c] B. Temme, G. Erker, J. Organomet. Chem. 1995, 488, 177. D. Röttger, G. Erker, R. Fröhlich, S. Kotila, J. Organomet. Chem. 1996, 518, 17. A. D. Horton, Organometallics 1996, 15, 2675.
24. For related methane elimination reactions see e.g.: [6a] A. Bertuleit, C. Fritze, G. Erker, R. Fröhlich, Organometallics 1997, 16, 2891. [6b] J. M. Meyer, C. J. Curtis, J. E. Bercaw, J. Am. Chem. Soc. 1983, 115, 2651. S. E. Buchwald, B. T. Watson, M. W. Wannamaker, C. Dewan, J. Am. Chem. Soc. 1989, 111, 4486. N. Coles, M. C. J. Harris, R. J. Whitby, J. Blagg, Organometallics 1994, 13, 190. [6c] B. Temme, G. Erker, J. Organomet. Chem. 1995, 488, 177. D. Röttger, G. Erker, R. Fröhlich, S. Kotila, J. Organomet. Chem. 1996, 518, 17. A. D. Horton, Organometallics 1996, 15, 2675.
25. For related methane elimination reactions see e.g.: [6a] A. Bertuleit, C. Fritze, G. Erker, R. Fröhlich, Organometallics 1997, 16, 2891. [6b] J. M. Meyer, C. J. Curtis, J. E. Bercaw, J. Am. Chem. Soc. 1983, 115, 2651. S. E. Buchwald, B. T. Watson, M. W. Wannamaker, C. Dewan, J. Am. Chem. Soc. 1989, 111, 4486. N. Coles, M. C. J. Harris, R. J. Whitby, J. Blagg, Organometallics 1994, 13, 190. [6c] B. Temme, G. Erker, J. Organomet. Chem. 1995, 488, 177. D. Röttger, G. Erker, R. Fröhlich, S. Kotila, J. Organomet. Chem. 1996, 518, 17. A. D. Horton, Organometallics 1996, 15, 2675.
26. For related methane elimination reactions see e.g.: [6a] A. Bertuleit, C. Fritze, G. Erker, R. Fröhlich, Organometallics 1997, 16, 2891. [6b] J. M. Meyer, C. J. Curtis, J. E. Bercaw, J. Am. Chem. Soc. 1983, 115, 2651. S. E. Buchwald, B. T. Watson, M. W. Wannamaker, C. Dewan, J. Am. Chem. Soc. 1989, 111, 4486. N. Coles, M. C. J. Harris, R. J. Whitby, J. Blagg, Organometallics 1994, 13, 190. [6c] B. Temme, G. Erker, J. Organomet. Chem. 1995, 488, 177. D. Röttger, G. Erker, R. Fröhlich, S. Kotila, J. Organomet. Chem. 1996, 518, 17. A. D. Horton, Organometallics 1996, 15, 2675.
27. For related methane elimination reactions see e.g.: [6a] A. Bertuleit, C. Fritze, G. Erker, R. Fröhlich, Organometallics 1997, 16, 2891. [6b] J. M. Meyer, C. J. Curtis, J. E. Bercaw, J. Am. Chem. Soc. 1983, 115, 2651. S. E. Buchwald, B. T. Watson, M. W. Wannamaker, C. Dewan, J. Am. Chem. Soc. 1989, 111, 4486. N. Coles, M. C. J. Harris, R. J. Whitby, J. Blagg, Organometallics 1994, 13, 190. [6c] B. Temme, G. Erker, J. Organomet. Chem. 1995, 488, 177. D. Röttger, G. Erker, R. Fröhlich, S. Kotila, J. Organomet. Chem. 1996, 518, 17. A. D. Horton, Organometallics 1996, 15, 2675.
28. For related methane elimination reactions see e.g.: [6a] A. Bertuleit, C. Fritze, G. Erker, R. Fröhlich, Organometallics 1997, 16, 2891. [6b] J. M. Meyer, C. J. Curtis, J. E. Bercaw, J. Am. Chem. Soc. 1983, 115, 2651. S. E. Buchwald, B. T. Watson, M. W. Wannamaker, C. Dewan, J. Am. Chem. Soc. 1989, 111, 4486. N. Coles, M. C. J. Harris, R. J. Whitby, J. Blagg, Organometallics 1994, 13, 190. [6c] B. Temme, G. Erker, J. Organomet. Chem. 1995, 488, 177. D. Röttger, G. Erker, R. Fröhlich, S. Kotila, J. Organomet. Chem. 1996, 518, 17. A. D. Horton, Organometallics 1996, 15, 2675.
29. For related methane elimination reactions see e.g.: [6a] A. Bertuleit, C. Fritze, G. Erker, R. Fröhlich, Organometallics 1997, 16, 2891. [6b] J. M. Meyer, C. J. Curtis, J. E. Bercaw, J. Am. Chem. Soc. 1983, 115, 2651. S. E. Buchwald, B. T. Watson, M. W. Wannamaker, C. Dewan, J. Am. Chem. Soc. 1989, 111, 4486. N. Coles, M. C. J. Harris, R. J. Whitby, J. Blagg, Organometallics 1994, 13, 190. [6c] B. Temme, G. Erker, J. Organomet. Chem. 1995, 488, 177. D. Röttger, G. Erker, R. Fröhlich, S. Kotila, J. Organomet. Chem. 1996, 518, 17. A. D. Horton, Organometallics 1996, 15, 2675.
30. For other examples of amidate (and amidinate) ligands at Zr see: [7a] G. Erker, K. Berg, J. Organomet. Chem. 1984, 263, 37. S. Gambarotta, S. Strogolo, C. Floriani, A. Chiesi-Villa, C. Guastini, J. Am. Chem. Soc. 1985, 107, 6278; Inorg. Chem. 1985, 24, 654. M. Vivanco, J. Ruiz, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Organometallics 1993, 12, 1794. [7b] R. Duchateau, A. Meetsma, H. J. Teuben, Organometallics 1996, 15, 1565. R. Duchateau, C. T. van Wee, A. Meetsma, P. T. van Duijnen, H. J. Teuben, Organometallics 1996, 15, 2279. R. Kempe, S. Brenner, P. Arndt, Organometallics 1996, 15, 1071. D. Walther, R. Fischer, M. Friedrich, P. Gebhardt, H. Görls, Chem. Ber. 1996, 129, 1389. A. Littke, N. Sleiman, C. Bensimon, D. S. Richeson, G. P. A. Yap, S. J. Brown, Organometallics 1998, 17, 446. J. R. Hagadorn, J. Arnold, Angew. Chem. 1998, 110, 1813; Angew. Chem. Int. Ed. Engl. 1998, 37, 1729.
31. For other examples of amidate (and amidinate) ligands at Zr see: [7a] G. Erker, K. Berg, J. Organomet. Chem. 1984, 263, 37. S. Gambarotta, S. Strogolo, C. Floriani, A. Chiesi-Villa, C. Guastini, J. Am. Chem. Soc. 1985, 107, 6278; Inorg. Chem. 1985, 24, 654. M. Vivanco, J. Ruiz, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Organometallics 1993, 12, 1794. [7b] R. Duchateau, A. Meetsma, H. J. Teuben, Organometallics 1996, 15, 1565. R. Duchateau, C. T. van Wee, A. Meetsma, P. T. van Duijnen, H. J. Teuben, Organometallics 1996, 15, 2279. R. Kempe, S. Brenner, P. Arndt, Organometallics 1996, 15, 1071. D. Walther, R. Fischer, M. Friedrich, P. Gebhardt, H. Görls, Chem. Ber. 1996, 129, 1389. A. Littke, N. Sleiman, C. Bensimon, D. S. Richeson, G. P. A. Yap, S. J. Brown, Organometallics 1998, 17, 446. J. R. Hagadorn, J. Arnold, Angew. Chem. 1998, 110, 1813; Angew. Chem. Int. Ed. Engl. 1998, 37, 1729.
32. For other examples of amidate (and amidinate) ligands at Zr see: [7a] G. Erker, K. Berg, J. Organomet. Chem. 1984, 263, 37. S. Gambarotta, S. Strogolo, C. Floriani, A. Chiesi-Villa, C. Guastini, J. Am. Chem. Soc. 1985, 107, 6278; Inorg. Chem. 1985, 24, 654. M. Vivanco, J. Ruiz, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Organometallics 1993, 12, 1794. [7b] R. Duchateau, A. Meetsma, H. J. Teuben, Organometallics 1996, 15, 1565. R. Duchateau, C. T. van Wee, A. Meetsma, P. T. van Duijnen, H. J. Teuben, Organometallics 1996, 15, 2279. R. Kempe, S. Brenner, P. Arndt, Organometallics 1996, 15, 1071. D. Walther, R. Fischer, M. Friedrich, P. Gebhardt, H. Görls, Chem. Ber. 1996, 129, 1389. A. Littke, N. Sleiman, C. Bensimon, D. S. Richeson, G. P. A. Yap, S. J. Brown, Organometallics 1998, 17, 446. J. R. Hagadorn, J. Arnold, Angew. Chem. 1998, 110, 1813; Angew. Chem. Int. Ed. Engl. 1998, 37, 1729.
33. For other examples of amidate (and amidinate) ligands at Zr see: [7a] G. Erker, K. Berg, J. Organomet. Chem. 1984, 263, 37. S. Gambarotta, S. Strogolo, C. Floriani, A. Chiesi-Villa, C. Guastini, J. Am. Chem. Soc. 1985, 107, 6278; Inorg. Chem. 1985, 24, 654. M. Vivanco, J. Ruiz, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Organometallics 1993, 12, 1794. [7b] R. Duchateau, A. Meetsma, H. J. Teuben, Organometallics 1996, 15, 1565. R. Duchateau, C. T. van Wee, A. Meetsma, P. T. van Duijnen, H. J. Teuben, Organometallics 1996, 15, 2279. R. Kempe, S. Brenner, P. Arndt, Organometallics 1996, 15, 1071. D. Walther, R. Fischer, M. Friedrich, P. Gebhardt, H. Görls, Chem. Ber. 1996, 129, 1389. A. Littke, N. Sleiman, C. Bensimon, D. S. Richeson, G. P. A. Yap, S. J. Brown, Organometallics 1998, 17, 446. J. R. Hagadorn, J. Arnold, Angew. Chem. 1998, 110, 1813; Angew. Chem. Int. Ed. Engl. 1998, 37, 1729.
34. For other examples of amidate (and amidinate) ligands at Zr see: [7a] G. Erker, K. Berg, J. Organomet. Chem. 1984, 263, 37. S. Gambarotta, S. Strogolo, C. Floriani, A. Chiesi-Villa, C. Guastini, J. Am. Chem. Soc. 1985, 107, 6278; Inorg. Chem. 1985, 24, 654. M. Vivanco, J. Ruiz, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Organometallics 1993, 12, 1794. [7b] R. Duchateau, A. Meetsma, H. J. Teuben, Organometallics 1996, 15, 1565. R. Duchateau, C. T. van Wee, A. Meetsma, P. T. van Duijnen, H. J. Teuben, Organometallics 1996, 15, 2279. R. Kempe, S. Brenner, P. Arndt, Organometallics 1996, 15, 1071. D. Walther, R. Fischer, M. Friedrich, P. Gebhardt, H. Görls, Chem. Ber. 1996, 129, 1389. A. Littke, N. Sleiman, C. Bensimon, D. S. Richeson, G. P. A. Yap, S. J. Brown, Organometallics 1998, 17, 446. J. R. Hagadorn, J. Arnold, Angew. Chem. 1998, 110, 1813; Angew. Chem. Int. Ed. Engl. 1998, 37, 1729.
35. For other examples of amidate (and amidinate) ligands at Zr see: [7a] G. Erker, K. Berg, J. Organomet. Chem. 1984, 263, 37. S. Gambarotta, S. Strogolo, C. Floriani, A. Chiesi-Villa, C. Guastini, J. Am. Chem. Soc. 1985, 107, 6278; Inorg. Chem. 1985, 24, 654. M. Vivanco, J. Ruiz, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Organometallics 1993, 12, 1794. [7b] R. Duchateau, A. Meetsma, H. J. Teuben, Organometallics 1996, 15, 1565. R. Duchateau, C. T. van Wee, A. Meetsma, P. T. van Duijnen, H. J. Teuben, Organometallics 1996, 15, 2279. R. Kempe, S. Brenner, P. Arndt, Organometallics 1996, 15, 1071. D. Walther, R. Fischer, M. Friedrich, P. Gebhardt, H. Görls, Chem. Ber. 1996, 129, 1389. A. Littke, N. Sleiman, C. Bensimon, D. S. Richeson, G. P. A. Yap, S. J. Brown, Organometallics 1998, 17, 446. J. R. Hagadorn, J. Arnold, Angew. Chem. 1998, 110, 1813; Angew. Chem. Int. Ed. Engl. 1998, 37, 1729.
36. For other examples of amidate (and amidinate) ligands at Zr see: [7a] G. Erker, K. Berg, J. Organomet. Chem. 1984, 263, 37. S. Gambarotta, S. Strogolo, C. Floriani, A. Chiesi-Villa, C. Guastini, J. Am. Chem. Soc. 1985, 107, 6278; Inorg. Chem. 1985, 24, 654. M. Vivanco, J. Ruiz, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Organometallics 1993, 12, 1794. [7b] R. Duchateau, A. Meetsma, H. J. Teuben, Organometallics 1996, 15, 1565. R. Duchateau, C. T. van Wee, A. Meetsma, P. T. van Duijnen, H. J. Teuben, Organometallics 1996, 15, 2279. R. Kempe, S. Brenner, P. Arndt, Organometallics 1996, 15, 1071. D. Walther, R. Fischer, M. Friedrich, P. Gebhardt, H. Görls, Chem. Ber. 1996, 129, 1389. A. Littke, N. Sleiman, C. Bensimon, D. S. Richeson, G. P. A. Yap, S. J. Brown, Organometallics 1998, 17, 446. J. R. Hagadorn, J. Arnold, Angew. Chem. 1998, 110, 1813; Angew. Chem. Int. Ed. Engl. 1998, 37, 1729.
37. For other examples of amidate (and amidinate) ligands at Zr see: [7a] G. Erker, K. Berg, J. Organomet. Chem. 1984, 263, 37. S. Gambarotta, S. Strogolo, C. Floriani, A. Chiesi-Villa, C. Guastini, J. Am. Chem. Soc. 1985, 107, 6278; Inorg. Chem. 1985, 24, 654. M. Vivanco, J. Ruiz, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Organometallics 1993, 12, 1794. [7b] R. Duchateau, A. Meetsma, H. J. Teuben, Organometallics 1996, 15, 1565. R. Duchateau, C. T. van Wee, A. Meetsma, P. T. van Duijnen, H. J. Teuben, Organometallics 1996, 15, 2279. R. Kempe, S. Brenner, P. Arndt, Organometallics 1996, 15, 1071. D. Walther, R. Fischer, M. Friedrich, P. Gebhardt, H. Görls, Chem. Ber. 1996, 129, 1389. A. Littke, N. Sleiman, C. Bensimon, D. S. Richeson, G. P. A. Yap, S. J. Brown, Organometallics 1998, 17, 446. J. R. Hagadorn, J. Arnold, Angew. Chem. 1998, 110, 1813; Angew. Chem. Int. Ed. Engl. 1998, 37, 1729.
38. For other examples of amidate (and amidinate) ligands at Zr see: [7a] G. Erker, K. Berg, J. Organomet. Chem. 1984, 263, 37. S. Gambarotta, S. Strogolo, C. Floriani, A. Chiesi-Villa, C. Guastini, J. Am. Chem. Soc. 1985, 107, 6278; Inorg. Chem. 1985, 24, 654. M. Vivanco, J. Ruiz, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Organometallics 1993, 12, 1794. [7b] R. Duchateau, A. Meetsma, H. J. Teuben, Organometallics 1996, 15, 1565. R. Duchateau, C. T. van Wee, A. Meetsma, P. T. van Duijnen, H. J. Teuben, Organometallics 1996, 15, 2279. R. Kempe, S. Brenner, P. Arndt, Organometallics 1996, 15, 1071. D. Walther, R. Fischer, M. Friedrich, P. Gebhardt, H. Görls, Chem. Ber. 1996, 129, 1389. A. Littke, N. Sleiman, C. Bensimon, D. S. Richeson, G. P. A. Yap, S. J. Brown, Organometallics 1998, 17, 446. J. R. Hagadorn, J. Arnold, Angew. Chem. 1998, 110, 1813; Angew. Chem. Int. Ed. Engl. 1998, 37, 1729.
39. For other examples of amidate (and amidinate) ligands at Zr see: [7a] G. Erker, K. Berg, J. Organomet. Chem. 1984, 263, 37. S. Gambarotta, S. Strogolo, C. Floriani, A. Chiesi-Villa, C. Guastini, J. Am. Chem. Soc. 1985, 107, 6278; Inorg. Chem. 1985, 24, 654. M. Vivanco, J. Ruiz, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Organometallics 1993, 12, 1794. [7b] R. Duchateau, A. Meetsma, H. J. Teuben, Organometallics 1996, 15, 1565. R. Duchateau, C. T. van Wee, A. Meetsma, P. T. van Duijnen, H. J. Teuben, Organometallics 1996, 15, 2279. R. Kempe, S. Brenner, P. Arndt, Organometallics 1996, 15, 1071. D. Walther, R. Fischer, M. Friedrich, P. Gebhardt, H. Görls, Chem. Ber. 1996, 129, 1389. A. Littke, N. Sleiman, C. Bensimon, D. S. Richeson, G. P. A. Yap, S. J. Brown, Organometallics 1998, 17, 446. J. R. Hagadorn, J. Arnold, Angew. Chem. 1998, 110, 1813; Angew. Chem. Int. Ed. Engl. 1998, 37, 1729.
40. For other examples of amidate (and amidinate) ligands at Zr see: [7a] G. Erker, K. Berg, J. Organomet. Chem. 1984, 263, 37. S. Gambarotta, S. Strogolo, C. Floriani, A. Chiesi-Villa, C. Guastini, J. Am. Chem. Soc. 1985, 107, 6278; Inorg. Chem. 1985, 24, 654. M. Vivanco, J. Ruiz, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Organometallics 1993, 12, 1794. [7b] R. Duchateau, A. Meetsma, H. J. Teuben, Organometallics 1996, 15, 1565. R. Duchateau, C. T. van Wee, A. Meetsma, P. T. van Duijnen, H. J. Teuben, Organometallics 1996, 15, 2279. R. Kempe, S. Brenner, P. Arndt, Organometallics 1996, 15, 1071. D. Walther, R. Fischer, M. Friedrich, P. Gebhardt, H. Görls, Chem. Ber. 1996, 129, 1389. A. Littke, N. Sleiman, C. Bensimon, D. S. Richeson, G. P. A. Yap, S. J. Brown, Organometallics 1998, 17, 446. J. R. Hagadorn, J. Arnold, Angew. Chem. 1998, 110, 1813; Angew. Chem. Int. Ed. Engl. 1998, 37, 1729.
41. Prepared by treatment of the amino acid or peptide ester with trichloromethyl chloroformate ("phosgene dimer"): S. Goldschmidt, M. Wick, Justus Liebes Ann. Chem. 1952, 575, 217. Y. Iwakura, K. Uno, S. Kang, J. Org. Chem. 1965, 30, 1158. H. Jeschkeit, G. Losse, K. Neubert, Chem. Ber. 1966, 99, 2803. J. S. Nowick, N. A. Powell, T. M. Nguyen, G. Noronha, J. Org. Chem. 1992, 57, 7364.
42. Prepared by treatment of the amino acid or peptide ester with trichloromethyl chloroformate ("phosgene dimer"): S. Goldschmidt, M. Wick, Justus Liebes Ann. Chem. 1952, 575, 217. Y. Iwakura, K. Uno, S. Kang, J. Org. Chem. 1965, 30, 1158. H. Jeschkeit, G. Losse, K. Neubert, Chem. Ber. 1966, 99, 2803. J. S. Nowick, N. A. Powell, T. M. Nguyen, G. Noronha, J. Org. Chem. 1992, 57, 7364.
43. Prepared by treatment of the amino acid or peptide ester with trichloromethyl chloroformate ("phosgene dimer"): S. Goldschmidt, M. Wick, Justus Liebes Ann. Chem. 1952, 575, 217. Y. Iwakura, K. Uno, S. Kang, J. Org. Chem. 1965, 30, 1158. H. Jeschkeit, G. Losse, K. Neubert, Chem. Ber. 1966, 99, 2803. J. S. Nowick, N. A. Powell, T. M. Nguyen, G. Noronha, J. Org. Chem. 1992, 57, 7364.
44. Prepared by treatment of the amino acid or peptide ester with trichloromethyl chloroformate ("phosgene dimer"): S. Goldschmidt, M. Wick, Justus Liebes Ann. Chem. 1952, 575, 217. Y. Iwakura, K. Uno, S. Kang, J. Org. Chem. 1965, 30, 1158. H. Jeschkeit, G. Losse, K. Neubert, Chem. Ber. 1966, 99, 2803. J. S. Nowick, N. A. Powell, T. M. Nguyen, G. Noronha, J. Org. Chem. 1992, 57, 7364.
45. The oligopeptide derivatives were prepared by conventional methods: M. Bodanszky, Peptide Chemistry, Springer, Berlin, 1993. M. Bodanszky, A. Bodanszky, The Practice of Peptide Synthesis, Springer, Berlin, 1994. L. A. Carpino, M. Beyermann, H. Wenschuh, M. Bienert, Acc. Chem. Res. 1996, 29, 268, and references cited in these articles.
46. The oligopeptide derivatives were prepared by conventional methods: M. Bodanszky, Peptide Chemistry, Springer, Berlin, 1993. M. Bodanszky, A. Bodanszky, The Practice of Peptide Synthesis, Springer, Berlin, 1994. L. A. Carpino, M. Beyermann, H. Wenschuh, M. Bienert, Acc. Chem. Res. 1996, 29, 268, and references cited in these articles.
47. The oligopeptide derivatives were prepared by conventional methods: M. Bodanszky, Peptide Chemistry, Springer, Berlin, 1993. M. Bodanszky, A. Bodanszky, The Practice of Peptide Synthesis, Springer, Berlin, 1994. L. A. Carpino, M. Beyermann, H. Wenschuh, M. Bienert, Acc. Chem. Res. 1996, 29, 268, and references cited in these articles.
48. S. Braun, H. Kalinowski, S. Berger, 100 and More Basic NMR Experiments, VCH, Weinheim, 1996, and references cited therein.
49. [11a] Y. Ariyoshi, Bull. Chem. Soc. Jpn. 1984, 57, 3197.
50. [11b] J. C. Sheehan, G. P. Hess, J. Am. Chem. Soc. 1955, 77, 1067. R. König. W. Geiger, Chem. Ber. 1970, 103, 788, 2024, 2034.
51. [11b] J. C. Sheehan, G. P. Hess, J. Am. Chem. Soc. 1955, 77, 1067. R. König. W. Geiger, Chem. Ber. 1970, 103, 788, 2024, 2034.