Catalytic formation of aziridines from imines. Characterisation of an intermediate in SnCl4-catalysed aziridination and mechanistic considerations

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 7, 1997, Pages 1347-1350

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

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0347170998     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (34)

1. For reviews about aziridines see e.g.: (a) A. Padwa and A. D. Woolhouse, in Comprehensive Heterocyclic Chemistry, eds. A. R. Katritzky and C.W. Rees, Pergamon, Oxford, 1984, vol. 7, p. 47; (b) J. Backes, in Houben-Weyl: Methoden der Organischen Chemie, ed. D. Klamann, Thieme, Stuttgart, 1992, vol. E, 16C, p. 370; (c) D. Tanner, Angew. Chem., Int. Ed. Engl., 1994, 33, 599; (d) H. M. I. Osborn and J. S. Sweeney, Tetrahedron: Asymmetry, 1997, 8, 1693.
2. For reviews about aziridines see e.g.: (a) A. Padwa and A. D. Woolhouse, in Comprehensive Heterocyclic Chemistry, eds. A. R. Katritzky and C.W. Rees, Pergamon, Oxford, 1984, vol. 7, p. 47; (b) J. Backes, in Houben-Weyl: Methoden der Organischen Chemie, ed. D. Klamann, Thieme, Stuttgart, 1992, vol. E, 16C, p. 370; (c) D. Tanner, Angew. Chem., Int. Ed. Engl., 1994, 33, 599; (d) H. M. I. Osborn and J. S. Sweeney, Tetrahedron: Asymmetry, 1997, 8, 1693.
3. For reviews about aziridines see e.g.: (a) A. Padwa and A. D. Woolhouse, in Comprehensive Heterocyclic Chemistry, eds. A. R. Katritzky and C.W. Rees, Pergamon, Oxford, 1984, vol. 7, p. 47; (b) J. Backes, in Houben-Weyl: Methoden der Organischen Chemie, ed. D. Klamann, Thieme, Stuttgart, 1992, vol. E, 16C, p. 370; (c) D. Tanner, Angew. Chem., Int. Ed. Engl., 1994, 33, 599; (d) H. M. I. Osborn and J. S. Sweeney, Tetrahedron: Asymmetry, 1997, 8, 1693.
4. For reviews about aziridines see e.g.: (a) A. Padwa and A. D. Woolhouse, in Comprehensive Heterocyclic Chemistry, eds. A. R. Katritzky and C.W. Rees, Pergamon, Oxford, 1984, vol. 7, p. 47; (b) J. Backes, in Houben-Weyl: Methoden der Organischen Chemie, ed. D. Klamann, Thieme, Stuttgart, 1992, vol. E, 16C, p. 370; (c) D. Tanner, Angew. Chem., Int. Ed. Engl., 1994, 33, 599; (d) H. M. I. Osborn and J. S. Sweeney, Tetrahedron: Asymmetry, 1997, 8, 1693.
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19. For other metal-catalysed reactions leading to aziridines from alkenes, see e.g.: (a) D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Am. Chem. Soc., 1994, 116, 2742; (b) J. Org. Chem., 1991, 56, 6744; (c) D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson and D. M. Barnes, J. Am. Chem. Soc., 1993, 115, 5328; (d) D. A. Evans, K. A. Woerpel, M. M. Hinman and M. M. Faul, J. Am. Chem. Soc., 1991, 113, 726; (e) A. M. Harm, J. G. Knight and G. Stemp, Tetrahedron Lett., 1996, 37, 6189; (f) Z. Li, K. R. Conser and E. N. Jacobsen, J. Am. Chem. Soc., 1993, 115, 5326; (g) W. Zhang, N. H. Lee and E. N. Jacobsen, J. Am. Chem. Soc., 1994, 116, 425; (h) Z. Li, R. W. Quan and E. N. Jacobsen, J. Am. Chem. Soc., 1995, 117, 5889; (i) J.-P. Mahy, G. Bedi, P. Battioni and D. Mansuy, J. Chem. Soc., Perkin Trans. 2, 1988, 1517; (j) K. J. O'Conner, S.-J. Wey and C. J. Burrows, Tetrahedron Lett., 1992, 33, 1001; (k) K. Noda, N. Hosoya, R. Irie, Y. Ito and T. Katsuki, Synlett, 1993, 469; (l) P. Müller, C. Baud and Y. Jacquier, Tetrahedron, 1996, 52, 1543.
20. For other metal-catalysed reactions leading to aziridines from alkenes, see e.g.: (a) D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Am. Chem. Soc., 1994, 116, 2742; (b) J. Org. Chem., 1991, 56, 6744; (c) D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson and D. M. Barnes, J. Am. Chem. Soc., 1993, 115, 5328; (d) D. A. Evans, K. A. Woerpel, M. M. Hinman and M. M. Faul, J. Am. Chem. Soc., 1991, 113, 726; (e) A. M. Harm, J. G. Knight and G. Stemp, Tetrahedron Lett., 1996, 37, 6189; (f) Z. Li, K. R. Conser and E. N. Jacobsen, J. Am. Chem. Soc., 1993, 115, 5326; (g) W. Zhang, N. H. Lee and E. N. Jacobsen, J. Am. Chem. Soc., 1994, 116, 425; (h) Z. Li, R. W. Quan and E. N. Jacobsen, J. Am. Chem. Soc., 1995, 117, 5889; (i) J.-P. Mahy, G. Bedi, P. Battioni and D. Mansuy, J. Chem. Soc., Perkin Trans. 2, 1988, 1517; (j) K. J. O'Conner, S.-J. Wey and C. J. Burrows, Tetrahedron Lett., 1992, 33, 1001; (k) K. Noda, N. Hosoya, R. Irie, Y. Ito and T. Katsuki, Synlett, 1993, 469; (l) P. Müller, C. Baud and Y. Jacquier, Tetrahedron, 1996, 52, 1543.
21. For other metal-catalysed reactions leading to aziridines from alkenes, see e.g.: (a) D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Am. Chem. Soc., 1994, 116, 2742; (b) J. Org. Chem., 1991, 56, 6744; (c) D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson and D. M. Barnes, J. Am. Chem. Soc., 1993, 115, 5328; (d) D. A. Evans, K. A. Woerpel, M. M. Hinman and M. M. Faul, J. Am. Chem. Soc., 1991, 113, 726; (e) A. M. Harm, J. G. Knight and G. Stemp, Tetrahedron Lett., 1996, 37, 6189; (f) Z. Li, K. R. Conser and E. N. Jacobsen, J. Am. Chem. Soc., 1993, 115, 5326; (g) W. Zhang, N. H. Lee and E. N. Jacobsen, J. Am. Chem. Soc., 1994, 116, 425; (h) Z. Li, R. W. Quan and E. N. Jacobsen, J. Am. Chem. Soc., 1995, 117, 5889; (i) J.-P. Mahy, G. Bedi, P. Battioni and D. Mansuy, J. Chem. Soc., Perkin Trans. 2, 1988, 1517; (j) K. J. O'Conner, S.-J. Wey and C. J. Burrows, Tetrahedron Lett., 1992, 33, 1001; (k) K. Noda, N. Hosoya, R. Irie, Y. Ito and T. Katsuki, Synlett, 1993, 469; (l) P. Müller, C. Baud and Y. Jacquier, Tetrahedron, 1996, 52, 1543.
22. For other metal-catalysed reactions leading to aziridines from alkenes, see e.g.: (a) D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Am. Chem. Soc., 1994, 116, 2742; (b) J. Org. Chem., 1991, 56, 6744; (c) D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson and D. M. Barnes, J. Am. Chem. Soc., 1993, 115, 5328; (d) D. A. Evans, K. A. Woerpel, M. M. Hinman and M. M. Faul, J. Am. Chem. Soc., 1991, 113, 726; (e) A. M. Harm, J. G. Knight and G. Stemp, Tetrahedron Lett., 1996, 37, 6189; (f) Z. Li, K. R. Conser and E. N. Jacobsen, J. Am. Chem. Soc., 1993, 115, 5326; (g) W. Zhang, N. H. Lee and E. N. Jacobsen, J. Am. Chem. Soc., 1994, 116, 425; (h) Z. Li, R. W. Quan and E. N. Jacobsen, J. Am. Chem. Soc., 1995, 117, 5889; (i) J.-P. Mahy, G. Bedi, P. Battioni and D. Mansuy, J. Chem. Soc., Perkin Trans. 2, 1988, 1517; (j) K. J. O'Conner, S.-J. Wey and C. J. Burrows, Tetrahedron Lett., 1992, 33, 1001; (k) K. Noda, N. Hosoya, R. Irie, Y. Ito and T. Katsuki, Synlett, 1993, 469; (l) P. Müller, C. Baud and Y. Jacquier, Tetrahedron, 1996, 52, 1543.
23. For other metal-catalysed reactions leading to aziridines from alkenes, see e.g.: (a) D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Am. Chem. Soc., 1994, 116, 2742; (b) J. Org. Chem., 1991, 56, 6744; (c) D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson and D. M. Barnes, J. Am. Chem. Soc., 1993, 115, 5328; (d) D. A. Evans, K. A. Woerpel, M. M. Hinman and M. M. Faul, J. Am. Chem. Soc., 1991, 113, 726; (e) A. M. Harm, J. G. Knight and G. Stemp, Tetrahedron Lett., 1996, 37, 6189; (f) Z. Li, K. R. Conser and E. N. Jacobsen, J. Am. Chem. Soc., 1993, 115, 5326; (g) W. Zhang, N. H. Lee and E. N. Jacobsen, J. Am. Chem. Soc., 1994, 116, 425; (h) Z. Li, R. W. Quan and E. N. Jacobsen, J. Am. Chem. Soc., 1995, 117, 5889; (i) J.-P. Mahy, G. Bedi, P. Battioni and D. Mansuy, J. Chem. Soc., Perkin Trans. 2, 1988, 1517; (j) K. J. O'Conner, S.-J. Wey and C. J. Burrows, Tetrahedron Lett., 1992, 33, 1001; (k) K. Noda, N. Hosoya, R. Irie, Y. Ito and T. Katsuki, Synlett, 1993, 469; (l) P. Müller, C. Baud and Y. Jacquier, Tetrahedron, 1996, 52, 1543.
24. For other metal-catalysed reactions leading to aziridines from alkenes, see e.g.: (a) D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Am. Chem. Soc., 1994, 116, 2742; (b) J. Org. Chem., 1991, 56, 6744; (c) D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson and D. M. Barnes, J. Am. Chem. Soc., 1993, 115, 5328; (d) D. A. Evans, K. A. Woerpel, M. M. Hinman and M. M. Faul, J. Am. Chem. Soc., 1991, 113, 726; (e) A. M. Harm, J. G. Knight and G. Stemp, Tetrahedron Lett., 1996, 37, 6189; (f) Z. Li, K. R. Conser and E. N. Jacobsen, J. Am. Chem. Soc., 1993, 115, 5326; (g) W. Zhang, N. H. Lee and E. N. Jacobsen, J. Am. Chem. Soc., 1994, 116, 425; (h) Z. Li, R. W. Quan and E. N. Jacobsen, J. Am. Chem. Soc., 1995, 117, 5889; (i) J.-P. Mahy, G. Bedi, P. Battioni and D. Mansuy, J. Chem. Soc., Perkin Trans. 2, 1988, 1517; (j) K. J. O'Conner, S.-J. Wey and C. J. Burrows, Tetrahedron Lett., 1992, 33, 1001; (k) K. Noda, N. Hosoya, R. Irie, Y. Ito and T. Katsuki, Synlett, 1993, 469; (l) P. Müller, C. Baud and Y. Jacquier, Tetrahedron, 1996, 52, 1543.
25. For other metal-catalysed reactions leading to aziridines from alkenes, see e.g.: (a) D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Am. Chem. Soc., 1994, 116, 2742; (b) J. Org. Chem., 1991, 56, 6744; (c) D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson and D. M. Barnes, J. Am. Chem. Soc., 1993, 115, 5328; (d) D. A. Evans, K. A. Woerpel, M. M. Hinman and M. M. Faul, J. Am. Chem. Soc., 1991, 113, 726; (e) A. M. Harm, J. G. Knight and G. Stemp, Tetrahedron Lett., 1996, 37, 6189; (f) Z. Li, K. R. Conser and E. N. Jacobsen, J. Am. Chem. Soc., 1993, 115, 5326; (g) W. Zhang, N. H. Lee and E. N. Jacobsen, J. Am. Chem. Soc., 1994, 116, 425; (h) Z. Li, R. W. Quan and E. N. Jacobsen, J. Am. Chem. Soc., 1995, 117, 5889; (i) J.-P. Mahy, G. Bedi, P. Battioni and D. Mansuy, J. Chem. Soc., Perkin Trans. 2, 1988, 1517; (j) K. J. O'Conner, S.-J. Wey and C. J. Burrows, Tetrahedron Lett., 1992, 33, 1001; (k) K. Noda, N. Hosoya, R. Irie, Y. Ito and T. Katsuki, Synlett, 1993, 469; (l) P. Müller, C. Baud and Y. Jacquier, Tetrahedron, 1996, 52, 1543.
26. For other metal-catalysed reactions leading to aziridines from alkenes, see e.g.: (a) D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Am. Chem. Soc., 1994, 116, 2742; (b) J. Org. Chem., 1991, 56, 6744; (c) D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson and D. M. Barnes, J. Am. Chem. Soc., 1993, 115, 5328; (d) D. A. Evans, K. A. Woerpel, M. M. Hinman and M. M. Faul, J. Am. Chem. Soc., 1991, 113, 726; (e) A. M. Harm, J. G. Knight and G. Stemp, Tetrahedron Lett., 1996, 37, 6189; (f) Z. Li, K. R. Conser and E. N. Jacobsen, J. Am. Chem. Soc., 1993, 115, 5326; (g) W. Zhang, N. H. Lee and E. N. Jacobsen, J. Am. Chem. Soc., 1994, 116, 425; (h) Z. Li, R. W. Quan and E. N. Jacobsen, J. Am. Chem. Soc., 1995, 117, 5889; (i) J.-P. Mahy, G. Bedi, P. Battioni and D. Mansuy, J. Chem. Soc., Perkin Trans. 2, 1988, 1517; (j) K. J. O'Conner, S.-J. Wey and C. J. Burrows, Tetrahedron Lett., 1992, 33, 1001; (k) K. Noda, N. Hosoya, R. Irie, Y. Ito and T. Katsuki, Synlett, 1993, 469; (l) P. Müller, C. Baud and Y. Jacquier, Tetrahedron, 1996, 52, 1543.
27. For other metal-catalysed reactions leading to aziridines from alkenes, see e.g.: (a) D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Am. Chem. Soc., 1994, 116, 2742; (b) J. Org. Chem., 1991, 56, 6744; (c) D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson and D. M. Barnes, J. Am. Chem. Soc., 1993, 115, 5328; (d) D. A. Evans, K. A. Woerpel, M. M. Hinman and M. M. Faul, J. Am. Chem. Soc., 1991, 113, 726; (e) A. M. Harm, J. G. Knight and G. Stemp, Tetrahedron Lett., 1996, 37, 6189; (f) Z. Li, K. R. Conser and E. N. Jacobsen, J. Am. Chem. Soc., 1993, 115, 5326; (g) W. Zhang, N. H. Lee and E. N. Jacobsen, J. Am. Chem. Soc., 1994, 116, 425; (h) Z. Li, R. W. Quan and E. N. Jacobsen, J. Am. Chem. Soc., 1995, 117, 5889; (i) J.-P. Mahy, G. Bedi, P. Battioni and D. Mansuy, J. Chem. Soc., Perkin Trans. 2, 1988, 1517; (j) K. J. O'Conner, S.-J. Wey and C. J. Burrows, Tetrahedron Lett., 1992, 33, 1001; (k) K. Noda, N. Hosoya, R. Irie, Y. Ito and T. Katsuki, Synlett, 1993, 469; (l) P. Müller, C. Baud and Y. Jacquier, Tetrahedron, 1996, 52, 1543.
28. For other metal-catalysed reactions leading to aziridines from alkenes, see e.g.: (a) D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Am. Chem. Soc., 1994, 116, 2742; (b) J. Org. Chem., 1991, 56, 6744; (c) D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson and D. M. Barnes, J. Am. Chem. Soc., 1993, 115, 5328; (d) D. A. Evans, K. A. Woerpel, M. M. Hinman and M. M. Faul, J. Am. Chem. Soc., 1991, 113, 726; (e) A. M. Harm, J. G. Knight and G. Stemp, Tetrahedron Lett., 1996, 37, 6189; (f) Z. Li, K. R. Conser and E. N. Jacobsen, J. Am. Chem. Soc., 1993, 115, 5326; (g) W. Zhang, N. H. Lee and E. N. Jacobsen, J. Am. Chem. Soc., 1994, 116, 425; (h) Z. Li, R. W. Quan and E. N. Jacobsen, J. Am. Chem. Soc., 1995, 117, 5889; (i) J.-P. Mahy, G. Bedi, P. Battioni and D. Mansuy, J. Chem. Soc., Perkin Trans. 2, 1988, 1517; (j) K. J. O'Conner, S.-J. Wey and C. J. Burrows, Tetrahedron Lett., 1992, 33, 1001; (k) K. Noda, N. Hosoya, R. Irie, Y. Ito and T. Katsuki, Synlett, 1993, 469; (l) P. Müller, C. Baud and Y. Jacquier, Tetrahedron, 1996, 52, 1543.
29. For other metal-catalysed reactions leading to aziridines from alkenes, see e.g.: (a) D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Am. Chem. Soc., 1994, 116, 2742; (b) J. Org. Chem., 1991, 56, 6744; (c) D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson and D. M. Barnes, J. Am. Chem. Soc., 1993, 115, 5328; (d) D. A. Evans, K. A. Woerpel, M. M. Hinman and M. M. Faul, J. Am. Chem. Soc., 1991, 113, 726; (e) A. M. Harm, J. G. Knight and G. Stemp, Tetrahedron Lett., 1996, 37, 6189; (f) Z. Li, K. R. Conser and E. N. Jacobsen, J. Am. Chem. Soc., 1993, 115, 5326; (g) W. Zhang, N. H. Lee and E. N. Jacobsen, J. Am. Chem. Soc., 1994, 116, 425; (h) Z. Li, R. W. Quan and E. N. Jacobsen, J. Am. Chem. Soc., 1995, 117, 5889; (i) J.-P. Mahy, G. Bedi, P. Battioni and D. Mansuy, J. Chem. Soc., Perkin Trans. 2, 1988, 1517; (j) K. J. O'Conner, S.-J. Wey and C. J. Burrows, Tetrahedron Lett., 1992, 33, 1001; (k) K. Noda, N. Hosoya, R. Irie, Y. Ito and T. Katsuki, Synlett, 1993, 469; (l) P. Müller, C. Baud and Y. Jacquier, Tetrahedron, 1996, 52, 1543.
30. For other metal-catalysed reactions leading to aziridines from alkenes, see e.g.: (a) D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Am. Chem. Soc., 1994, 116, 2742; (b) J. Org. Chem., 1991, 56, 6744; (c) D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson and D. M. Barnes, J. Am. Chem. Soc., 1993, 115, 5328; (d) D. A. Evans, K. A. Woerpel, M. M. Hinman and M. M. Faul, J. Am. Chem. Soc., 1991, 113, 726; (e) A. M. Harm, J. G. Knight and G. Stemp, Tetrahedron Lett., 1996, 37, 6189; (f) Z. Li, K. R. Conser and E. N. Jacobsen, J. Am. Chem. Soc., 1993, 115, 5326; (g) W. Zhang, N. H. Lee and E. N. Jacobsen, J. Am. Chem. Soc., 1994, 116, 425; (h) Z. Li, R. W. Quan and E. N. Jacobsen, J. Am. Chem. Soc., 1995, 117, 5889; (i) J.-P. Mahy, G. Bedi, P. Battioni and D. Mansuy, J. Chem. Soc., Perkin Trans. 2, 1988, 1517; (j) K. J. O'Conner, S.-J. Wey and C. J. Burrows, Tetrahedron Lett., 1992, 33, 1001; (k) K. Noda, N. Hosoya, R. Irie, Y. Ito and T. Katsuki, Synlett, 1993, 469; (l) P. Müller, C. Baud and Y. Jacquier, Tetrahedron, 1996, 52, 1543.
31. K. G. Rasmussen, R. G. Hazell and K. A. Jørgensen, Chem. Commun., 1997, 1103.
32. A search in the CCDC data file for a series of very similar imines gave an average C=N bond length of 1.28 Å.
33. 4 coordinated to a nitrogen and an oxygen atom of an organic ligand(s): P. Domiano, A. Musatti, N. Nardelli, C. Pelizzi and G. Predieri, Inorg. Chim. Acta, 1980, 9, 38.
34. L. A. Bigalow and H. Eatough, Org. Synth., 1932, coll. vol. I, 73.