Crystal structure of an imine-TiCl4 complex formed in catalytic aziridination reactions. scope and mechanistic considerations

Acta Chemica Scandinavica

Volumn 52, Issue 8, 1998, Pages 1056-1059

  Rasmussen, Kaare G ^a   Hazell, Rita G ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009137622     PISSN: 0904213X     EISSN: None     Source Type: Journal    
DOI: 10.3891/acta.chem.scand.52-1056     Document Type: Article

References (36)

1. For reviews about aziridines see, e.g.; (a) Padwa, A. and Woodhouse, A. D. In: Katitzky, A. R. and Rees, C. W., Eds., Comprehensive Heterocyclic Chemistry, Pergamon, Oxford 1984, Vol. 7, p. 47; (b) Backes, J. In: Klomann, D., Ed., Houben-Wevl: Methoden der Organischen Chemie, Thieme, Stuttgart 1992, Vol. E, 16C, p. 370; (c) Tanner, D. Angew. Chem., Int. Ed. Engl. 33 (1994) 599; (d) Osborn, H. M. I. and Sweeney, J. Tetrahedron: Asymmetry 8 (1997) 1693.
2. For reviews about aziridines see, e.g.; (a) Padwa, A. and Woodhouse, A. D. In: Katitzky, A. R. and Rees, C. W., Eds., Comprehensive Heterocyclic Chemistry, Pergamon, Oxford 1984, Vol. 7, p. 47; (b) Backes, J. In: Klomann, D., Ed., Houben-Wevl: Methoden der Organischen Chemie, Thieme, Stuttgart 1992, Vol. E, 16C, p. 370; (c) Tanner, D. Angew. Chem., Int. Ed. Engl. 33 (1994) 599; (d) Osborn, H. M. I. and Sweeney, J. Tetrahedron: Asymmetry 8 (1997) 1693.
3. For reviews about aziridines see, e.g.; (a) Padwa, A. and Woodhouse, A. D. In: Katitzky, A. R. and Rees, C. W., Eds., Comprehensive Heterocyclic Chemistry, Pergamon, Oxford 1984, Vol. 7, p. 47; (b) Backes, J. In: Klomann, D., Ed., Houben-Wevl: Methoden der Organischen Chemie, Thieme, Stuttgart 1992, Vol. E, 16C, p. 370; (c) Tanner, D. Angew. Chem., Int. Ed. Engl. 33 (1994) 599; (d) Osborn, H. M. I. and Sweeney, J. Tetrahedron: Asymmetry 8 (1997) 1693.
4. For reviews about aziridines see, e.g.; (a) Padwa, A. and Woodhouse, A. D. In: Katitzky, A. R. and Rees, C. W., Eds., Comprehensive Heterocyclic Chemistry, Pergamon, Oxford 1984, Vol. 7, p. 47; (b) Backes, J. In: Klomann, D., Ed., Houben-Wevl: Methoden der Organischen Chemie, Thieme, Stuttgart 1992, Vol. E, 16C, p. 370; (c) Tanner, D. Angew. Chem., Int. Ed. Engl. 33 (1994) 599; (d) Osborn, H. M. I. and Sweeney, J. Tetrahedron: Asymmetry 8 (1997) 1693.
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15. (J) Wang, D.-K., Dai, L.-X. and Hou, X.-L. J. Chem. Soc., Chem. Commun. (1997) 1231;
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18. (m) Ha, H.-J., Suh, J.-M., Kant, K.-H., Ahn, Y.-G. and Han, O. Tetrahedron 54 (1998) 851.
19. For other metal-catalyzed reactions leading to aziridines, see e.g., (a) Evans, D. A., Faul, M. M. and Bilodeau, M. T. J. Am. Chem. Soc. 116 (1994) 2742; (b) J. Org. Chem 56 (1991) 6744; (c) Evans, D. A., Faul, M. M., Bilodeau, M. T., Anderson, B. A. and Barnes, D. M. J. Am. Chem. Soc. 115 (1993) 5328; (d) Evans, D. A., Woerpel, K. A., Hinman, M. M. and Faul, M. M. J. Am. Chem. Soc. 113 (1991) 726; (e) Harm, A. M., Knight, J. G. and Stemp, G. Tetrahedron Lett. 37 (1996) 6189; (f) Li, Z., Conser, K. R. and Jacobsen, E. N. J. Am. Chem. Soc. 115 (1993) 5326; (g) Zhang, W., Lee, N. H. and Jacobsen, E. N. J. Am. Chem. Soc. 116 (1994) 425; (h) Li, Z., Quan, R. W. and Jacobsen, E. N. J. Am Chem. Soc. 117 (1995) 5889; (i) Mahy, J.-P., Bedi, G., Battioni, P. and Mansuy, D. J. Chem. Soc., Perkin Trans. 2 (1988) 1517; (j) O'Conner, K. J., Wey, S.-J. and Burrows, C. J. Tetrahedron Lett. 33 (1992) 1001; (k) Noda, K., Hosoya, N., Irie, R., Ito, Y. and Katsuki, T. Synlett (1993) 469; (l) Müller, P., Baud, C. and Jacqueier, Y. Tetrahedron 52 (1996) 1543.
20. For other metal-catalyzed reactions leading to aziridines, see e.g., (a) Evans, D. A., Faul, M. M. and Bilodeau, M. T. J. Am. Chem. Soc. 116 (1994) 2742; (b) J. Org. Chem 56 (1991) 6744; (c) Evans, D. A., Faul, M. M., Bilodeau, M. T., Anderson, B. A. and Barnes, D. M. J. Am. Chem. Soc. 115 (1993) 5328; (d) Evans, D. A., Woerpel, K. A., Hinman, M. M. and Faul, M. M. J. Am. Chem. Soc. 113 (1991) 726; (e) Harm, A. M., Knight, J. G. and Stemp, G. Tetrahedron Lett. 37 (1996) 6189; (f) Li, Z., Conser, K. R. and Jacobsen, E. N. J. Am. Chem. Soc. 115 (1993) 5326; (g) Zhang, W., Lee, N. H. and Jacobsen, E. N. J. Am. Chem. Soc. 116 (1994) 425; (h) Li, Z., Quan, R. W. and Jacobsen, E. N. J. Am Chem. Soc. 117 (1995) 5889; (i) Mahy, J.-P., Bedi, G., Battioni, P. and Mansuy, D. J. Chem. Soc., Perkin Trans. 2 (1988) 1517; (j) O'Conner, K. J., Wey, S.-J. and Burrows, C. J. Tetrahedron Lett. 33 (1992) 1001; (k) Noda, K., Hosoya, N., Irie, R., Ito, Y. and Katsuki, T. Synlett (1993) 469; (l) Müller, P., Baud, C. and Jacqueier, Y. Tetrahedron 52 (1996) 1543.
21. For other metal-catalyzed reactions leading to aziridines, see e.g., (a) Evans, D. A., Faul, M. M. and Bilodeau, M. T. J. Am. Chem. Soc. 116 (1994) 2742; (b) J. Org. Chem 56 (1991) 6744; (c) Evans, D. A., Faul, M. M., Bilodeau, M. T., Anderson, B. A. and Barnes, D. M. J. Am. Chem. Soc. 115 (1993) 5328; (d) Evans, D. A., Woerpel, K. A., Hinman, M. M. and Faul, M. M. J. Am. Chem. Soc. 113 (1991) 726; (e) Harm, A. M., Knight, J. G. and Stemp, G. Tetrahedron Lett. 37 (1996) 6189; (f) Li, Z., Conser, K. R. and Jacobsen, E. N. J. Am. Chem. Soc. 115 (1993) 5326; (g) Zhang, W., Lee, N. H. and Jacobsen, E. N. J. Am. Chem. Soc. 116 (1994) 425; (h) Li, Z., Quan, R. W. and Jacobsen, E. N. J. Am Chem. Soc. 117 (1995) 5889; (i) Mahy, J.-P., Bedi, G., Battioni, P. and Mansuy, D. J. Chem. Soc., Perkin Trans. 2 (1988) 1517; (j) O'Conner, K. J., Wey, S.-J. and Burrows, C. J. Tetrahedron Lett. 33 (1992) 1001; (k) Noda, K., Hosoya, N., Irie, R., Ito, Y. and Katsuki, T. Synlett (1993) 469; (l) Müller, P., Baud, C. and Jacqueier, Y. Tetrahedron 52 (1996) 1543.
22. For other metal-catalyzed reactions leading to aziridines, see e.g., (a) Evans, D. A., Faul, M. M. and Bilodeau, M. T. J. Am. Chem. Soc. 116 (1994) 2742; (b) J. Org. Chem 56 (1991) 6744; (c) Evans, D. A., Faul, M. M., Bilodeau, M. T., Anderson, B. A. and Barnes, D. M. J. Am. Chem. Soc. 115 (1993) 5328; (d) Evans, D. A., Woerpel, K. A., Hinman, M. M. and Faul, M. M. J. Am. Chem. Soc. 113 (1991) 726; (e) Harm, A. M., Knight, J. G. and Stemp, G. Tetrahedron Lett. 37 (1996) 6189; (f) Li, Z., Conser, K. R. and Jacobsen, E. N. J. Am. Chem. Soc. 115 (1993) 5326; (g) Zhang, W., Lee, N. H. and Jacobsen, E. N. J. Am. Chem. Soc. 116 (1994) 425; (h) Li, Z., Quan, R. W. and Jacobsen, E. N. J. Am Chem. Soc. 117 (1995) 5889; (i) Mahy, J.-P., Bedi, G., Battioni, P. and Mansuy, D. J. Chem. Soc., Perkin Trans. 2 (1988) 1517; (j) O'Conner, K. J., Wey, S.-J. and Burrows, C. J. Tetrahedron Lett. 33 (1992) 1001; (k) Noda, K., Hosoya, N., Irie, R., Ito, Y. and Katsuki, T. Synlett (1993) 469; (l) Müller, P., Baud, C. and Jacqueier, Y. Tetrahedron 52 (1996) 1543.
23. For other metal-catalyzed reactions leading to aziridines, see e.g., (a) Evans, D. A., Faul, M. M. and Bilodeau, M. T. J. Am. Chem. Soc. 116 (1994) 2742; (b) J. Org. Chem 56 (1991) 6744; (c) Evans, D. A., Faul, M. M., Bilodeau, M. T., Anderson, B. A. and Barnes, D. M. J. Am. Chem. Soc. 115 (1993) 5328; (d) Evans, D. A., Woerpel, K. A., Hinman, M. M. and Faul, M. M. J. Am. Chem. Soc. 113 (1991) 726; (e) Harm, A. M., Knight, J. G. and Stemp, G. Tetrahedron Lett. 37 (1996) 6189; (f) Li, Z., Conser, K. R. and Jacobsen, E. N. J. Am. Chem. Soc. 115 (1993) 5326; (g) Zhang, W., Lee, N. H. and Jacobsen, E. N. J. Am. Chem. Soc. 116 (1994) 425; (h) Li, Z., Quan, R. W. and Jacobsen, E. N. J. Am Chem. Soc. 117 (1995) 5889; (i) Mahy, J.-P., Bedi, G., Battioni, P. and Mansuy, D. J. Chem. Soc., Perkin Trans. 2 (1988) 1517; (j) O'Conner, K. J., Wey, S.-J. and Burrows, C. J. Tetrahedron Lett. 33 (1992) 1001; (k) Noda, K., Hosoya, N., Irie, R., Ito, Y. and Katsuki, T. Synlett (1993) 469; (l) Müller, P., Baud, C. and Jacqueier, Y. Tetrahedron 52 (1996) 1543.
24. For other metal-catalyzed reactions leading to aziridines, see e.g., (a) Evans, D. A., Faul, M. M. and Bilodeau, M. T. J. Am. Chem. Soc. 116 (1994) 2742; (b) J. Org. Chem 56 (1991) 6744; (c) Evans, D. A., Faul, M. M., Bilodeau, M. T., Anderson, B. A. and Barnes, D. M. J. Am. Chem. Soc. 115 (1993) 5328; (d) Evans, D. A., Woerpel, K. A., Hinman, M. M. and Faul, M. M. J. Am. Chem. Soc. 113 (1991) 726; (e) Harm, A. M., Knight, J. G. and Stemp, G. Tetrahedron Lett. 37 (1996) 6189; (f) Li, Z., Conser, K. R. and Jacobsen, E. N. J. Am. Chem. Soc. 115 (1993) 5326; (g) Zhang, W., Lee, N. H. and Jacobsen, E. N. J. Am. Chem. Soc. 116 (1994) 425; (h) Li, Z., Quan, R. W. and Jacobsen, E. N. J. Am Chem. Soc. 117 (1995) 5889; (i) Mahy, J.-P., Bedi, G., Battioni, P. and Mansuy, D. J. Chem. Soc., Perkin Trans. 2 (1988) 1517; (j) O'Conner, K. J., Wey, S.-J. and Burrows, C. J. Tetrahedron Lett. 33 (1992) 1001; (k) Noda, K., Hosoya, N., Irie, R., Ito, Y. and Katsuki, T. Synlett (1993) 469; (l) Müller, P., Baud, C. and Jacqueier, Y. Tetrahedron 52 (1996) 1543.
25. For other metal-catalyzed reactions leading to aziridines, see e.g., (a) Evans, D. A., Faul, M. M. and Bilodeau, M. T. J. Am. Chem. Soc. 116 (1994) 2742; (b) J. Org. Chem 56 (1991) 6744; (c) Evans, D. A., Faul, M. M., Bilodeau, M. T., Anderson, B. A. and Barnes, D. M. J. Am. Chem. Soc. 115 (1993) 5328; (d) Evans, D. A., Woerpel, K. A., Hinman, M. M. and Faul, M. M. J. Am. Chem. Soc. 113 (1991) 726; (e) Harm, A. M., Knight, J. G. and Stemp, G. Tetrahedron Lett. 37 (1996) 6189; (f) Li, Z., Conser, K. R. and Jacobsen, E. N. J. Am. Chem. Soc. 115 (1993) 5326; (g) Zhang, W., Lee, N. H. and Jacobsen, E. N. J. Am. Chem. Soc. 116 (1994) 425; (h) Li, Z., Quan, R. W. and Jacobsen, E. N. J. Am Chem. Soc. 117 (1995) 5889; (i) Mahy, J.-P., Bedi, G., Battioni, P. and Mansuy, D. J. Chem. Soc., Perkin Trans. 2 (1988) 1517; (j) O'Conner, K. J., Wey, S.-J. and Burrows, C. J. Tetrahedron Lett. 33 (1992) 1001; (k) Noda, K., Hosoya, N., Irie, R., Ito, Y. and Katsuki, T. Synlett (1993) 469; (l) Müller, P., Baud, C. and Jacqueier, Y. Tetrahedron 52 (1996) 1543.
26. For other metal-catalyzed reactions leading to aziridines, see e.g., (a) Evans, D. A., Faul, M. M. and Bilodeau, M. T. J. Am. Chem. Soc. 116 (1994) 2742; (b) J. Org. Chem 56 (1991) 6744; (c) Evans, D. A., Faul, M. M., Bilodeau, M. T., Anderson, B. A. and Barnes, D. M. J. Am. Chem. Soc. 115 (1993) 5328; (d) Evans, D. A., Woerpel, K. A., Hinman, M. M. and Faul, M. M. J. Am. Chem. Soc. 113 (1991) 726; (e) Harm, A. M., Knight, J. G. and Stemp, G. Tetrahedron Lett. 37 (1996) 6189; (f) Li, Z., Conser, K. R. and Jacobsen, E. N. J. Am. Chem. Soc. 115 (1993) 5326; (g) Zhang, W., Lee, N. H. and Jacobsen, E. N. J. Am. Chem. Soc. 116 (1994) 425; (h) Li, Z., Quan, R. W. and Jacobsen, E. N. J. Am Chem. Soc. 117 (1995) 5889; (i) Mahy, J.-P., Bedi, G., Battioni, P. and Mansuy, D. J. Chem. Soc., Perkin Trans. 2 (1988) 1517; (j) O'Conner, K. J., Wey, S.-J. and Burrows, C. J. Tetrahedron Lett. 33 (1992) 1001; (k) Noda, K., Hosoya, N., Irie, R., Ito, Y. and Katsuki, T. Synlett (1993) 469; (l) Müller, P., Baud, C. and Jacqueier, Y. Tetrahedron 52 (1996) 1543.
27. For other metal-catalyzed reactions leading to aziridines, see e.g., (a) Evans, D. A., Faul, M. M. and Bilodeau, M. T. J. Am. Chem. Soc. 116 (1994) 2742; (b) J. Org. Chem 56 (1991) 6744; (c) Evans, D. A., Faul, M. M., Bilodeau, M. T., Anderson, B. A. and Barnes, D. M. J. Am. Chem. Soc. 115 (1993) 5328; (d) Evans, D. A., Woerpel, K. A., Hinman, M. M. and Faul, M. M. J. Am. Chem. Soc. 113 (1991) 726; (e) Harm, A. M., Knight, J. G. and Stemp, G. Tetrahedron Lett. 37 (1996) 6189; (f) Li, Z., Conser, K. R. and Jacobsen, E. N. J. Am. Chem. Soc. 115 (1993) 5326; (g) Zhang, W., Lee, N. H. and Jacobsen, E. N. J. Am. Chem. Soc. 116 (1994) 425; (h) Li, Z., Quan, R. W. and Jacobsen, E. N. J. Am Chem. Soc. 117 (1995) 5889; (i) Mahy, J.-P., Bedi, G., Battioni, P. and Mansuy, D. J. Chem. Soc., Perkin Trans. 2 (1988) 1517; (j) O'Conner, K. J., Wey, S.-J. and Burrows, C. J. Tetrahedron Lett. 33 (1992) 1001; (k) Noda, K., Hosoya, N., Irie, R., Ito, Y. and Katsuki, T. Synlett (1993) 469; (l) Müller, P., Baud, C. and Jacqueier, Y. Tetrahedron 52 (1996) 1543.
28. For other metal-catalyzed reactions leading to aziridines, see e.g., (a) Evans, D. A., Faul, M. M. and Bilodeau, M. T. J. Am. Chem. Soc. 116 (1994) 2742; (b) J. Org. Chem 56 (1991) 6744; (c) Evans, D. A., Faul, M. M., Bilodeau, M. T., Anderson, B. A. and Barnes, D. M. J. Am. Chem. Soc. 115 (1993) 5328; (d) Evans, D. A., Woerpel, K. A., Hinman, M. M. and Faul, M. M. J. Am. Chem. Soc. 113 (1991) 726; (e) Harm, A. M., Knight, J. G. and Stemp, G. Tetrahedron Lett. 37 (1996) 6189; (f) Li, Z., Conser, K. R. and Jacobsen, E. N. J. Am. Chem. Soc. 115 (1993) 5326; (g) Zhang, W., Lee, N. H. and Jacobsen, E. N. J. Am. Chem. Soc. 116 (1994) 425; (h) Li, Z., Quan, R. W. and Jacobsen, E. N. J. Am Chem. Soc. 117 (1995) 5889; (i) Mahy, J.-P., Bedi, G., Battioni, P. and Mansuy, D. J. Chem. Soc., Perkin Trans. 2 (1988) 1517; (j) O'Conner, K. J., Wey, S.-J. and Burrows, C. J. Tetrahedron Lett. 33 (1992) 1001; (k) Noda, K., Hosoya, N., Irie, R., Ito, Y. and Katsuki, T. Synlett (1993) 469; (l) Müller, P., Baud, C. and Jacqueier, Y. Tetrahedron 52 (1996) 1543.
29. For other metal-catalyzed reactions leading to aziridines, see e.g., (a) Evans, D. A., Faul, M. M. and Bilodeau, M. T. J. Am. Chem. Soc. 116 (1994) 2742; (b) J. Org. Chem 56 (1991) 6744; (c) Evans, D. A., Faul, M. M., Bilodeau, M. T., Anderson, B. A. and Barnes, D. M. J. Am. Chem. Soc. 115 (1993) 5328; (d) Evans, D. A., Woerpel, K. A., Hinman, M. M. and Faul, M. M. J. Am. Chem. Soc. 113 (1991) 726; (e) Harm, A. M., Knight, J. G. and Stemp, G. Tetrahedron Lett. 37 (1996) 6189; (f) Li, Z., Conser, K. R. and Jacobsen, E. N. J. Am. Chem. Soc. 115 (1993) 5326; (g) Zhang, W., Lee, N. H. and Jacobsen, E. N. J. Am. Chem. Soc. 116 (1994) 425; (h) Li, Z., Quan, R. W. and Jacobsen, E. N. J. Am Chem. Soc. 117 (1995) 5889; (i) Mahy, J.-P., Bedi, G., Battioni, P. and Mansuy, D. J. Chem. Soc., Perkin Trans. 2 (1988) 1517; (j) O'Conner, K. J., Wey, S.-J. and Burrows, C. J. Tetrahedron Lett. 33 (1992) 1001; (k) Noda, K., Hosoya, N., Irie, R., Ito, Y. and Katsuki, T. Synlett (1993) 469; (l) Müller, P., Baud, C. and Jacqueier, Y. Tetrahedron 52 (1996) 1543.
30. For other metal-catalyzed reactions leading to aziridines, see e.g., (a) Evans, D. A., Faul, M. M. and Bilodeau, M. T. J. Am. Chem. Soc. 116 (1994) 2742; (b) J. Org. Chem 56 (1991) 6744; (c) Evans, D. A., Faul, M. M., Bilodeau, M. T., Anderson, B. A. and Barnes, D. M. J. Am. Chem. Soc. 115 (1993) 5328; (d) Evans, D. A., Woerpel, K. A., Hinman, M. M. and Faul, M. M. J. Am. Chem. Soc. 113 (1991) 726; (e) Harm, A. M., Knight, J. G. and Stemp, G. Tetrahedron Lett. 37 (1996) 6189; (f) Li, Z., Conser, K. R. and Jacobsen, E. N. J. Am. Chem. Soc. 115 (1993) 5326; (g) Zhang, W., Lee, N. H. and Jacobsen, E. N. J. Am. Chem. Soc. 116 (1994) 425; (h) Li, Z., Quan, R. W. and Jacobsen, E. N. J. Am Chem. Soc. 117 (1995) 5889; (i) Mahy, J.-P., Bedi, G., Battioni, P. and Mansuy, D. J. Chem. Soc., Perkin Trans. 2 (1988) 1517; (j) O'Conner, K. J., Wey, S.-J. and Burrows, C. J. Tetrahedron Lett. 33 (1992) 1001; (k) Noda, K., Hosoya, N., Irie, R., Ito, Y. and Katsuki, T. Synlett (1993) 469; (l) Müller, P., Baud, C. and Jacqueier, Y. Tetrahedron 52 (1996) 1543.
31. Rasmussen, K. G., Hazell, R. G. and Jørgensen, K. A. J. Chem. Soc., Chem. Commun. (1997) 1103.
32. See eg., (a) Narasaka, K. Synthesis (1991) 1; (b) Kagan, H. B. and Riant, O. Chem. Rev. 92 (1992) 1007; (c) Diaz, L. C. J. Braz. Chem. Soc. 8 (1997) 289; (d) Gothelf, K. V. and Jørgensen, K. A. Chem. Rev. 98 (1998) 863.
33. See eg., (a) Narasaka, K. Synthesis (1991) 1; (b) Kagan, H. B. and Riant, O. Chem. Rev. 92 (1992) 1007; (c) Diaz, L. C. J. Braz. Chem. Soc. 8 (1997) 289; (d) Gothelf, K. V. and Jørgensen, K. A. Chem. Rev. 98 (1998) 863.
34. See eg., (a) Narasaka, K. Synthesis (1991) 1; (b) Kagan, H. B. and Riant, O. Chem. Rev. 92 (1992) 1007; (c) Diaz, L. C. J. Braz. Chem. Soc. 8 (1997) 289; (d) Gothelf, K. V. and Jørgensen, K. A. Chem. Rev. 98 (1998) 863.
35. See eg., (a) Narasaka, K. Synthesis (1991) 1; (b) Kagan, H. B. and Riant, O. Chem. Rev. 92 (1992) 1007; (c) Diaz, L. C. J. Braz. Chem. Soc. 8 (1997) 289; (d) Gothelf, K. V. and Jørgensen, K. A. Chem. Rev. 98 (1998) 863.
36. Gothelf, K. V., Hazell, R. G. and Jørgensen, K. A. J. Am. Chem. Soc. 117 (1995) 4435.