A New, Mild Synthesis of N-Sulfonyl Ketimines via the Palladium-Catalyzed Isomerization of Aziridines

Organic Letters

Volumn 5, Issue 24, 2003, Pages 4607-4610

  Wolfe, John P ^a   Ney, Joshua E ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; AZIRIDINE DERIVATIVE; ESTER; IMINE; KETONE DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; ISOMERISM; OXIDATION; SYNTHESIS;

EID: 0346150277     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0357651     Document Type: Article

References (41)

1. Weinreb, S. M. Top. Curr. Chem. 1997, 190, 131-184.
2. (a) Sisko, J.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 3037-3040.
3. (b) Boger, D. L.; Corbett, W. L.; Curran, T. T.; Kasper, A. M. J. Am. Chem. Soc. 1991, 113, 1713-1729.
4. (c) Abramovitch, R. A.; Shinkai, I.; Mavunkel, B. J.; More, K. M.; O'Connor, S.; Ooi, G. H.; Pennington, W. T.; Srinivasan, P. C.; Stowers, J. R. Tetrahedron 1996, 52, 3339-3354.
5. (d) McFarlane, A. K.; Thomas, G.; Whiting, A. Tetrahedron Lett. 1993, 34, 2379-2382.
6. (a) Trost, B. M.; Marrs, C. M. J. Am. Chem. Soc. 1993, 115, 6636-6645.
7. (b) Shigeru, Y.; Yanagawa, M.; Nakamura, E. Chem Lett. 1999, 879-880.
8. (a) Miyabe, H.; Ueda, M.; Naito, T. Chem. Commun. 2000, 2059-2060.
9. (b) Yamada, K.-i.; Fujihara, H.; Yamamoto, Y.; Miwa, Y.; Taga, T.; Tomioka, K. Org. Lett. 2002, 4, 3509-3511.
10. (c) Aggarwal, V. K.; Alonso, E.; Ferrara, M.; Spey, S. E. J. Org. Chem. 2002, 67, 2335-2344.
11. (d) Yamanaka, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 159-161.
12. (e) Sisko, J.; Weinreb, S. M. J. Org. Chem. 1990, 55, 393-395.
13. (f) Melnick, M. J.; Freyer, A. J.; Weinreb, S. M. Tetrahedron Lett. 1988, 29, 3891-3894.
14. Charette, A. B.; Giroux, A. Tetrahedron Lett. 1996, 37, 6669-6672.
15. (a) Lee, K. Y.; Lee, C. G.; Kim, J. N. Tetrahedron Lett. 2003, 44, 1231-1234 and references therein.
16. (b) Love, B. E.; Raje, P. S.; Williams, T. C., II. Synlett 1994, 493-494.
17. (c) Jennings, W. B.; Lovely, C. J. Tetrahedron 1991, 47, 5561-5568.
18. (d) Vishwakarma, L. C.; Stringer, O. D.; Davis, F. A. Org. Synth. 1987, 66, 203-208.
19. For preparation of enolizable tosyl aldimines using condensation methodology, see: Chemla, F.; Hebbe, V.; Normant, J.-F. Synthesis 2000, 75-77.
20. Trost, B. M.; Marrs, C. J. Org. Chem. 1991, 56, 6468-6470.
21. Georg, G. I.; Harriman, G. C. B.; Peterson, S. A. J. Org. Chem. 1995, 60, 7366-7368.
22. For synthesis of enolizable tosyl aldimines via photochemical rearrangement of naphtho[1,8-de]-dithiin-1-N-tosylsulfilimines, see: Fujii, T.; Kimura, T.; Furukawa, N. Tetrahedron Lett. 1995, 36, 1075-1078.
23. (a) Artman, G. D.; Bartolozzi, A.; Franck, R. W.; Weinreb, S. M. Synlett 2001, 232-233 and references therein.
24. (b) Brown, C.; Hudson, R. F.; Record, K. A. F. J. Chem. Soc., Perkin Trans. 2 1978, 822-828.
25. Boger, D. L.; Corbett, W. L. J. Org. Chem. 1992, 57, 4777-4780.
26. 2 or (bipy)Ni(COD). See: Lin, B. L.; Clough, C. R.; Hillhouse, G. L. J. Am. Chem. Soc. 2002, 124, 2890-2891.
27. (b) The oxidative addition of ethyleneimine to Pt(II) under acidic conditions has been previously described. See: Mitchenko, S. A.; Slinkin, S. M. ; Vdovichenko, A. N.; Zamashchikov, V. V. Metallorg. Khim. 1991, 4, 1031-1035.
28. The palladium-catalyzed isomerization of epoxides to ketones has been previously reported. See: (a) Suzuki, M.; Watanabe, A.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 2095-2096. (b) Kulasegaram, S.; Kulawiec, R. J. J. Org. Chem. 1997, 62, 6547-6561 and references therein.
29. The palladium-catalyzed isomerization of epoxides to ketones has been previously reported. See: (a) Suzuki, M.; Watanabe, A.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 2095-2096. (b) Kulasegaram, S.; Kulawiec, R. J. J. Org. Chem. 1997, 62, 6547-6561 and references therein.
30. 6 with 1 equiv of tricyclohexylphosphine in the absence of Pd.
31. For recent examples in catalytic reactions, see: (a) Butler, D. C. D.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887-5890. (b) Fugami, K.; Morizawa, Y.; Ishima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 857-860. (c) Aoyagi, K.; Nakamura, H.; Yamamoto, Y. J. Org. Chem. 2002, 67, 5977-5980. (d) Trost, B. M.; Fandrick, D. R. J. Am. Chem. Soc. 2003, 125, 11836-11837.
32. For recent examples in catalytic reactions, see: (a) Butler, D. C. D.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887-5890. (b) Fugami, K.; Morizawa, Y.; Ishima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 857-860. (c) Aoyagi, K.; Nakamura, H.; Yamamoto, Y. J. Org. Chem. 2002, 67, 5977-5980. (d) Trost, B. M.; Fandrick, D. R. J. Am. Chem. Soc. 2003, 125, 11836-11837.
33. For recent examples in catalytic reactions, see: (a) Butler, D. C. D.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887-5890. (b) Fugami, K.; Morizawa, Y.; Ishima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 857-860. (c) Aoyagi, K.; Nakamura, H.; Yamamoto, Y. J. Org. Chem. 2002, 67, 5977-5980. (d) Trost, B. M.; Fandrick, D. R. J. Am. Chem. Soc. 2003, 125, 11836-11837.
34. For recent examples in catalytic reactions, see: (a) Butler, D. C. D.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887-5890. (b) Fugami, K.; Morizawa, Y.; Ishima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 857-860. (c) Aoyagi, K.; Nakamura, H.; Yamamoto, Y. J. Org. Chem. 2002, 67, 5977-5980. (d) Trost, B. M.; Fandrick, D. R. J. Am. Chem. Soc. 2003, 125, 11836-11837.
35. 3 did effectively catalyze the isomerization of 1. However, chromatographic separation of the imine product from dba was very difficult.
36. Aziridines bearing N-benzyl or N-diphenylphosphoryl groups did not react under our standard conditions. The reaction of an N-boc aziridine proceeded very slowly, requiring 1 equiv 3 and >24 h at 80°C to reach completion.
37. N2 mechanism. See ref 13a.
38. Lewis acid mediated nucleophilic ring-opening reactions of N-tosyl-2-phenylaziridine typically afford products resulting from substitution at the benzylic position or mixtures of regioisomers. For recent examples, see: (a) Ungureanu, I.; Bologa, C.; Chayer, S.; Mann, A. Tetrahedron Lett. 1999, 40, 5315-5318. (b) Schneider, M. -R.; Klotz, P.; Ungureanu, I.; Mann, A.; Wermuth, C. -G. Tetrahedron Lett. 1999, 40, 3873-3876. (c) Sabitha, G.; Babu, R. S.; Rajkumar, M.; Reddy, C. S.; Yadav, J. S. Tetrahedron Lett. 2001, 42, 3955-3958.
39. Lewis acid mediated nucleophilic ring-opening reactions of N-tosyl-2-phenylaziridine typically afford products resulting from substitution at the benzylic position or mixtures of regioisomers. For recent examples, see: (a) Ungureanu, I.; Bologa, C.; Chayer, S.; Mann, A. Tetrahedron Lett. 1999, 40, 5315-5318. (b) Schneider, M. -R.; Klotz, P.; Ungureanu, I.; Mann, A.; Wermuth, C. -G. Tetrahedron Lett. 1999, 40, 3873-3876. (c) Sabitha, G.; Babu, R. S.; Rajkumar, M.; Reddy, C. S.; Yadav, J. S. Tetrahedron Lett. 2001, 42, 3955-3958.
40. Lewis acid mediated nucleophilic ring-opening reactions of N-tosyl-2-phenylaziridine typically afford products resulting from substitution at the benzylic position or mixtures of regioisomers. For recent examples, see: (a) Ungureanu, I.; Bologa, C.; Chayer, S.; Mann, A. Tetrahedron Lett. 1999, 40, 5315-5318. (b) Schneider, M. -R.; Klotz, P.; Ungureanu, I.; Mann, A.; Wermuth, C. -G. Tetrahedron Lett. 1999, 40, 3873-3876. (c) Sabitha, G.; Babu, R. S.; Rajkumar, M.; Reddy, C. S.; Yadav, J. S. Tetrahedron Lett. 2001, 42, 3955-3958.
41. Zhang, L.; Zetterberg, K. Organometallics 1991, 10, 3806-3813.