A unique and highly efficient method for catalytic olefin aziridination

Journal of the American Chemical Society

Volumn 124, Issue 46, 2002, Pages 13672-13673

  Guthikonda, Kiran ^a   Bois, J Du ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AZIRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; MOLECULAR INTERACTION; REACTION ANALYSIS; TECHNIQUE;

EID: 0037146032     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028253a     Document Type: Article

References (28)

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10. For general references on alkene aziridination, see: Jacobsen, E. N. In Comprehensive Asymmetric Catalysis: (a) Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 2, pp 607-618. (b) Müller, P. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JA1 Press Inc.: Greenwich, 1997; Vol. 2, pp 113-151. (c) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742-2753. For recent advances in aziridine synthesis, see: (d) Padwa, A.; Stengel, T. Org. Lett. 2002, 4, 2137-2139. (e) Gillespie, K. M.; Sanders, C. J.; O'Shaugnessy, P.; Westmoreland, I.; Thickitt, C. P.; Scott, P. J. Org. Chem. 2002, 67, 3450-3458. (f) Liang, J.-L.; Huang, J.-S.; Yu, X.-Q.; Zhu, N.; Che, C.-M. Chem.-Eur. J. 2002, 8, 1563-1572. (g) Siu, T.; Yudin, A. K. J. Am. Chem. Soc. 2002, 124, 530-531. (h) Dauban, P.; Sanière, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707-7708.
11. For general references on alkene aziridination, see: Jacobsen, E. N. In Comprehensive Asymmetric Catalysis: (a) Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 2, pp 607-618. (b) Müller, P. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JA1 Press Inc.: Greenwich, 1997; Vol. 2, pp 113-151. (c) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742-2753. For recent advances in aziridine synthesis, see: (d) Padwa, A.; Stengel, T. Org. Lett. 2002, 4, 2137-2139. (e) Gillespie, K. M.; Sanders, C. J.; O'Shaugnessy, P.; Westmoreland, I.; Thickitt, C. P.; Scott, P. J. Org. Chem. 2002, 67, 3450-3458. (f) Liang, J.-L.; Huang, J.-S.; Yu, X.-Q.; Zhu, N.; Che, C.-M. Chem.-Eur. J. 2002, 8, 1563-1572. (g) Siu, T.; Yudin, A. K. J. Am. Chem. Soc. 2002, 124, 530-531. (h) Dauban, P.; Sanière, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707-7708.
12. For general references on alkene aziridination, see: Jacobsen, E. N. In Comprehensive Asymmetric Catalysis: (a) Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 2, pp 607-618. (b) Müller, P. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JA1 Press Inc.: Greenwich, 1997; Vol. 2, pp 113-151. (c) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742-2753. For recent advances in aziridine synthesis, see: (d) Padwa, A.; Stengel, T. Org. Lett. 2002, 4, 2137-2139. (e) Gillespie, K. M.; Sanders, C. J.; O'Shaugnessy, P.; Westmoreland, I.; Thickitt, C. P.; Scott, P. J. Org. Chem. 2002, 67, 3450-3458. (f) Liang, J.-L.; Huang, J.-S.; Yu, X.-Q.; Zhu, N.; Che, C.-M. Chem.-Eur. J. 2002, 8, 1563-1572. (g) Siu, T.; Yudin, A. K. J. Am. Chem. Soc. 2002, 124, 530-531. (h) Dauban, P.; Sanière, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707-7708.
13. For general references on alkene aziridination, see: Jacobsen, E. N. In Comprehensive Asymmetric Catalysis: (a) Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 2, pp 607-618. (b) Müller, P. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JA1 Press Inc.: Greenwich, 1997; Vol. 2, pp 113-151. (c) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742-2753. For recent advances in aziridine synthesis, see: (d) Padwa, A.; Stengel, T. Org. Lett. 2002, 4, 2137-2139. (e) Gillespie, K. M.; Sanders, C. J.; O'Shaugnessy, P.; Westmoreland, I.; Thickitt, C. P.; Scott, P. J. Org. Chem. 2002, 67, 3450-3458. (f) Liang, J.-L.; Huang, J.-S.; Yu, X.-Q.; Zhu, N.; Che, C.-M. Chem.-Eur. J. 2002, 8, 1563-1572. (g) Siu, T.; Yudin, A. K. J. Am. Chem. Soc. 2002, 124, 530-531. (h) Dauban, P.; Sanière, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707-7708.
14. For general references on alkene aziridination, see: Jacobsen, E. N. In Comprehensive Asymmetric Catalysis: (a) Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 2, pp 607-618. (b) Müller, P. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JA1 Press Inc.: Greenwich, 1997; Vol. 2, pp 113-151. (c) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742-2753. For recent advances in aziridine synthesis, see: (d) Padwa, A.; Stengel, T. Org. Lett. 2002, 4, 2137-2139. (e) Gillespie, K. M.; Sanders, C. J.; O'Shaugnessy, P.; Westmoreland, I.; Thickitt, C. P.; Scott, P. J. Org. Chem. 2002, 67, 3450-3458. (f) Liang, J.-L.; Huang, J.-S.; Yu, X.-Q.; Zhu, N.; Che, C.-M. Chem.-Eur. J. 2002, 8, 1563-1572. (g) Siu, T.; Yudin, A. K. J. Am. Chem. Soc. 2002, 124, 530-531. (h) Dauban, P.; Sanière, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707-7708.
15. For general references on alkene aziridination, see: Jacobsen, E. N. In Comprehensive Asymmetric Catalysis: (a) Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 2, pp 607-618. (b) Müller, P. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JA1 Press Inc.: Greenwich, 1997; Vol. 2, pp 113-151. (c) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742-2753. For recent advances in aziridine synthesis, see: (d) Padwa, A.; Stengel, T. Org. Lett. 2002, 4, 2137-2139. (e) Gillespie, K. M.; Sanders, C. J.; O'Shaugnessy, P.; Westmoreland, I.; Thickitt, C. P.; Scott, P. J. Org. Chem. 2002, 67, 3450-3458. (f) Liang, J.-L.; Huang, J.-S.; Yu, X.-Q.; Zhu, N.; Che, C.-M. Chem.-Eur. J. 2002, 8, 1563-1572. (g) Siu, T.; Yudin, A. K. J. Am. Chem. Soc. 2002, 124, 530-531. (h) Dauban, P.; Sanière, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707-7708.
16. For general references on alkene aziridination, see: Jacobsen, E. N. In Comprehensive Asymmetric Catalysis: (a) Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 2, pp 607-618. (b) Müller, P. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JA1 Press Inc.: Greenwich, 1997; Vol. 2, pp 113-151. (c) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742-2753. For recent advances in aziridine synthesis, see: (d) Padwa, A.; Stengel, T. Org. Lett. 2002, 4, 2137-2139. (e) Gillespie, K. M.; Sanders, C. J.; O'Shaugnessy, P.; Westmoreland, I.; Thickitt, C. P.; Scott, P. J. Org. Chem. 2002, 67, 3450-3458. (f) Liang, J.-L.; Huang, J.-S.; Yu, X.-Q.; Zhu, N.; Che, C.-M. Chem.-Eur. J. 2002, 8, 1563-1572. (g) Siu, T.; Yudin, A. K. J. Am. Chem. Soc. 2002, 124, 530-531. (h) Dauban, P.; Sanière, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707-7708.
17. For general references on alkene aziridination, see: Jacobsen, E. N. In Comprehensive Asymmetric Catalysis: (a) Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 2, pp 607-618. (b) Müller, P. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JA1 Press Inc.: Greenwich, 1997; Vol. 2, pp 113-151. (c) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742-2753. For recent advances in aziridine synthesis, see: (d) Padwa, A.; Stengel, T. Org. Lett. 2002, 4, 2137-2139. (e) Gillespie, K. M.; Sanders, C. J.; O'Shaugnessy, P.; Westmoreland, I.; Thickitt, C. P.; Scott, P. J. Org. Chem. 2002, 67, 3450-3458. (f) Liang, J.-L.; Huang, J.-S.; Yu, X.-Q.; Zhu, N.; Che, C.-M. Chem.-Eur. J. 2002, 8, 1563-1572. (g) Siu, T.; Yudin, A. K. J. Am. Chem. Soc. 2002, 124, 530-531. (h) Dauban, P.; Sanière, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707-7708.
18. For recent reviews on applications of aziridines, see: (a) Zwanenburg, B.; ten Holte, P. Top. Curr. Chem. 2001, 216, 93-124.
19. (b) McCoull, W.; Davis, F. A. Synthesis 2000, 1347-1365.
20. 2Ar has been described previously, see: Müller, P.; Baud, C.; Jacquier, Y. Can. J. Chem. 1998, 76, 738-750 and references therein.
21. Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935-6936.
22. Analogous reactions of homoallyl sulfamate esters with Cu catalysts and PhI=O have appeared recently, see: Duran, F.; Leman, L.; Ghini, A.; Burton, G.; Dauban, P.; Dodd, R. H. Org. Lett. 2002, 4, 2481-2483. We have found that these conditions can be employed with 1 for intermolecular aziridination.
23. Barrett, A. G. M.; Betts, M. J.; Fenwick, A. J. Org. Chem. 1985. 50, 169-175.
24. 4 and used without purification (see the Supporting Information for details). This complex has been synthesized previously, see: Dennis, A. M.; Korp, J. D.; Bemal, I.; Howard, R. A.; Bear, J. L. Inorg. Chem. 1983, 22, 1522-1529.
25. 5Cl can be used with little diminution in product yields.
26. 2; see ref 5h.
27. The only exceptions that we have found to date are cyclohexene and cyclopentene, which give ∼ 1:1 and 2:1 mixtures of both the desired aziridine and the allylic insertion product, respectively.
28. 2 (AcOH) is sufficient to cleave reductively the p-(trifluoromethyl)benzyloxysulfonyl group.