Transition metal-catalyzed synthesis and reactivity of N-alkenyl aziridines

Organic Letters

Volumn 7, Issue 6, 2005, Pages 1161-1164

  Dalili, Shadi ^a   Yudin, Andrei K ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; ALKENYL GROUP; AZIRIDINE DERIVATIVE; BORONIC ACID DERIVATIVE; CYANIC ACID; ENAMINE; HALIDE; NITROGEN DERIVATIVE; PALLADIUM; SULFONE DERIVATIVE; TRANSITION ELEMENT;

ARTICLE; CATALYSIS; CATALYST; ELECTRON TRANSPORT; ENERGY YIELD; MOLECULAR INTERACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE;

EID: 18244368687     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050094n     Document Type: Article

References (42)

1. Rappoport, Z. In The Chemistry of Enamines; Wiley & Sons: New York, 1994; Vol. 2.
2. Stork, G.; Szmuszkovicz, J.; Terrell, R.; Brizzolara, A.; Landesman, H. J. Am. Chem. Soc. 1963, 85, 207.
3. Hickmott, P. W. Tetrahedron 1982, 38, 1975.
4. 2-triazolines, see: (i) Hassner, A.; Belinka, B. A.; Haber, M.; Munger, P. Tetrahedron Lett. 1981, 22, 1863.
5. 2-triazolines, see: (i) Hassner, A.; Belinka, B. A.; Haber, M.; Munger, P. Tetrahedron Lett. 1981, 22, 1863.
6. 2-triazolines, see: (i) Hassner, A.; Belinka, B. A.; Haber, M.; Munger, P. Tetrahedron Lett. 1981, 22, 1863.
7. 2-triazolines, see: (i) Hassner, A.; Belinka, B. A.; Haber, M.; Munger, P. Tetrahedron Lett. 1981, 22, 1863.
8. 2-triazolines, see: (i) Hassner, A.; Belinka, B. A.; Haber, M.; Munger, P. Tetrahedron Lett. 1981, 22, 1863.
9. 2-triazolines, see: (i) Hassner, A.; Belinka, B. A.; Haber, M.; Munger, P. Tetrahedron Lett. 1981, 22, 1863.
10. 2-triazolines, see: (i) Hassner, A.; Belinka, B. A.; Haber, M.; Munger, P. Tetrahedron Lett. 1981, 22, 1863.
11. 2-triazolines, see: (i) Hassner, A.; Belinka, B. A.; Haber, M.; Munger, P. Tetrahedron Lett. 1981, 22, 1863.
12. 2-triazolines, see: (i) Hassner, A.; Belinka, B. A.; Haber, M.; Munger, P. Tetrahedron Lett. 1981, 22, 1863.
13. Buist, G. J.; Lucas, H. S. J. Am. Chem. Soc. 1957, 79, 6157.
14. Sasaki, M.; Yudin, A. K. J. Am. Chem. Soc. 2003, 125, 14242.
15. For recent reviews, see: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J. F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (b) Hartwtig, J. F. Acc. Chem. Res. 1998, 31, 852. (c) Hartwig, J. F. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, Germany, 2000. (d) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 133. (e) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
16. For recent reviews, see: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J. F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (b) Hartwtig, J. F. Acc. Chem. Res. 1998, 31, 852. (c) Hartwig, J. F. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, Germany, 2000. (d) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 133. (e) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
17. For recent reviews, see: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J. F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (b) Hartwtig, J. F. Acc. Chem. Res. 1998, 31, 852. (c) Hartwig, J. F. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, Germany, 2000. (d) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 133. (e) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
18. For recent reviews, see: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J. F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (b) Hartwtig, J. F. Acc. Chem. Res. 1998, 31, 852. (c) Hartwig, J. F. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, Germany, 2000. (d) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 133. (e) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
19. For recent reviews, see: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J. F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (b) Hartwtig, J. F. Acc. Chem. Res. 1998, 31, 852. (c) Hartwig, J. F. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, Germany, 2000. (d) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 133. (e) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
20. For intermolecular palladium-catalyzed cross-coupling of amines with alkenyl bromides, see: (a) Barluenga, J.; Fernandez, M. A.; Aznar, F.; Valdes, C. Chem. Commun. 2002, 2362. (b) Barluenga, J.; Fernandez, M. A.; Aznar, F.; Valdes, C. Chem. Eur. J. 2004, 10, 494. For intramolecular palladium-catalyzed cross-coupling of alkenyl halide and β-lactam nitrogen, leading to a carbapenem skeleton, see: (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 111. (d) Kozawa, Y.; Mori, M. J. Org. Chem. 2003, 68, 3064. For palladium-catalyzed cross-coupling of azoles with alkenyl bromides, see: (e) Lebedev, A. Y.; Izmer, V. V.; Kazyul'kin, D. N.; Beletskaya, I. P.; Voskoboynikov, A. Z. Org. Lett. 2002, 4, 623.
21. For intermolecular palladium-catalyzed cross-coupling of amines with alkenyl bromides, see: (a) Barluenga, J.; Fernandez, M. A.; Aznar, F.; Valdes, C. Chem. Commun. 2002, 2362. (b) Barluenga, J.; Fernandez, M. A.; Aznar, F.; Valdes, C. Chem. Eur. J. 2004, 10, 494. For intramolecular palladium-catalyzed cross-coupling of alkenyl halide and β-lactam nitrogen, leading to a carbapenem skeleton, see: (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 111. (d) Kozawa, Y.; Mori, M. J. Org. Chem. 2003, 68, 3064. For palladium-catalyzed cross-coupling of azoles with alkenyl bromides, see: (e) Lebedev, A. Y.; Izmer, V. V.; Kazyul'kin, D. N.; Beletskaya, I. P.; Voskoboynikov, A. Z. Org. Lett. 2002, 4, 623.
22. For intermolecular palladium-catalyzed cross-coupling of amines with alkenyl bromides, see: (a) Barluenga, J.; Fernandez, M. A.; Aznar, F.; Valdes, C. Chem. Commun. 2002, 2362. (b) Barluenga, J.; Fernandez, M. A.; Aznar, F.; Valdes, C. Chem. Eur. J. 2004, 10, 494. For intramolecular palladium-catalyzed cross-coupling of alkenyl halide and β-lactam nitrogen, leading to a carbapenem skeleton, see: (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 111. (d) Kozawa, Y.; Mori, M. J. Org. Chem. 2003, 68, 3064. For palladium-catalyzed cross-coupling of azoles with alkenyl bromides, see: (e) Lebedev, A. Y.; Izmer, V. V.; Kazyul'kin, D. N.; Beletskaya, I. P.; Voskoboynikov, A. Z. Org. Lett. 2002, 4, 623.
23. For intermolecular palladium-catalyzed cross-coupling of amines with alkenyl bromides, see: (a) Barluenga, J.; Fernandez, M. A.; Aznar, F.; Valdes, C. Chem. Commun. 2002, 2362. (b) Barluenga, J.; Fernandez, M. A.; Aznar, F.; Valdes, C. Chem. Eur. J. 2004, 10, 494. For intramolecular palladium-catalyzed cross-coupling of alkenyl halide and β-lactam nitrogen, leading to a carbapenem skeleton, see: (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 111. (d) Kozawa, Y.; Mori, M. J. Org. Chem. 2003, 68, 3064. For palladium-catalyzed cross-coupling of azoles with alkenyl bromides, see: (e) Lebedev, A. Y.; Izmer, V. V.; Kazyul'kin, D. N.; Beletskaya, I. P.; Voskoboynikov, A. Z. Org. Lett. 2002, 4, 623.
24. For intermolecular palladium-catalyzed cross-coupling of amines with alkenyl bromides, see: (a) Barluenga, J.; Fernandez, M. A.; Aznar, F.; Valdes, C. Chem. Commun. 2002, 2362. (b) Barluenga, J.; Fernandez, M. A.; Aznar, F.; Valdes, C. Chem. Eur. J. 2004, 10, 494. For intramolecular palladium-catalyzed cross-coupling of alkenyl halide and β-lactam nitrogen, leading to a carbapenem skeleton, see: (c) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 111. (d) Kozawa, Y.; Mori, M. J. Org. Chem. 2003, 68, 3064. For palladium-catalyzed cross-coupling of azoles with alkenyl bromides, see: (e) Lebedev, A. Y.; Izmer, V. V.; Kazyul'kin, D. N.; Beletskaya, I. P.; Voskoboynikov, A. Z. Org. Lett. 2002, 4, 623.
25. tBu (1.4 equiv), and dry, degassed toluene. After the mixture was stirred at room temperature for about 10 min, the alkenyl bromide (1 equiv) and the aziridine (1.1 equiv) were added under argon, and the flask was immersed in an oil bath and heated to 90°C with stirring until the starting alkenyl bromide had been completely consumed as judged by GC and TLC analysis. All reactions were generally complete after overnight stirring. The mixture was then allowed to cool to room temperature, diluted with hexanes, and filtered through Celite. The solvent was evaporated in vacuo, and the residue was redissolved in hexanes, filtered through Celite, concentrated under reduced pressure, and dried under high vacuum to remove any excess aziridine. This afforded a residue that consisted of the crude N-alkenyl aziridine, which was purified further by Kugelrohr distillation under high vacuum (dependent on the boiling point and amount of product obtained) or by column chromatography on alumina.
26. Hara, S.; Dojo, H.; Takinami, S.; Suzuki, A. Tetrahedron Lett. 1983, 24, 731.
27. S,3R)-(+)-3-Methyl-2-phenylaziridine was synthesized according to published procedure; see: Galindo, A.; Orea, L. F.; Gnecco, D.; Enriquez, R. G.; Toscano, R. A.; Reynolds, W. F. Tetrahedron: Asymmetry 1997, 8, 2877.
28. For Pd-catalyzed isomerization of cis-olefins, see: Yu, J.; Gaunt, M. J.; Spencer, J. B. J. Org. Chem. 2002, 67, 4627.
29. Seko, S.; Tani, N. Tetrahedron Lett. 1998, 39, 8117.
30. We have observed lack of reactivity of carbonyl-containing aziridines in other transition metal-catalyzed processes: Chen, G.; Yudin, A. K. Unpublished results.
31. For some recent examples of amination of aryl halides, see: (a) Gajare, A. S.; Toyota, K.; Yoshifuji, M.; Ozawa, F. Chem. Commun. 2004, 17, 1994. (b) Lu, Z.; Twilg, R. J.; Huang, S. D. Tetrahedron Lett. 2003, 44, 628. (c) Enguehard, C.; Allouchi, H.; Guieffer, A.; Buchwald, S. L. J. Org. Chem. 2003, 68, 4367. (d) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793. (e) Kelkar, A. A.; Patil, N. M.; Chaudhari, R. V. Tetrahedron Lett. 2002, 58, 7943. (f) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581. (g) Clement, J. B.; Hayes, J. F.; Sheldrake, H. M.; Sheldrake, P. W.; Wells, A. S. Synlett, 2001, 9, 1423. (h) Satoh, T.; Matsue, R.; Fujii, T.; Morikawa, S. Tetrahedron, 2001, 57, 3891.
32. For some recent examples of amination of aryl halides, see: (a) Gajare, A. S.; Toyota, K.; Yoshifuji, M.; Ozawa, F. Chem. Commun. 2004, 17, 1994. (b) Lu, Z.; Twilg, R. J.; Huang, S. D. Tetrahedron Lett. 2003, 44, 628. (c) Enguehard, C.; Allouchi, H.; Guieffer, A.; Buchwald, S. L. J. Org. Chem. 2003, 68, 4367. (d) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793. (e) Kelkar, A. A.; Patil, N. M.; Chaudhari, R. V. Tetrahedron Lett. 2002, 58, 7943. (f) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581. (g) Clement, J. B.; Hayes, J. F.; Sheldrake, H. M.; Sheldrake, P. W.; Wells, A. S. Synlett, 2001, 9, 1423. (h) Satoh, T.; Matsue, R.; Fujii, T.; Morikawa, S. Tetrahedron, 2001, 57, 3891.
33. For some recent examples of amination of aryl halides, see: (a) Gajare, A. S.; Toyota, K.; Yoshifuji, M.; Ozawa, F. Chem. Commun. 2004, 17, 1994. (b) Lu, Z.; Twilg, R. J.; Huang, S. D. Tetrahedron Lett. 2003, 44, 628. (c) Enguehard, C.; Allouchi, H.; Guieffer, A.; Buchwald, S. L. J. Org. Chem. 2003, 68, 4367. (d) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793. (e) Kelkar, A. A.; Patil, N. M.; Chaudhari, R. V. Tetrahedron Lett. 2002, 58, 7943. (f) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581. (g) Clement, J. B.; Hayes, J. F.; Sheldrake, H. M.; Sheldrake, P. W.; Wells, A. S. Synlett, 2001, 9, 1423. (h) Satoh, T.; Matsue, R.; Fujii, T.; Morikawa, S. Tetrahedron, 2001, 57, 3891.
34. For some recent examples of amination of aryl halides, see: (a) Gajare, A. S.; Toyota, K.; Yoshifuji, M.; Ozawa, F. Chem. Commun. 2004, 17, 1994. (b) Lu, Z.; Twilg, R. J.; Huang, S. D. Tetrahedron Lett. 2003, 44, 628. (c) Enguehard, C.; Allouchi, H.; Guieffer, A.; Buchwald, S. L. J. Org. Chem. 2003, 68, 4367. (d) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793. (e) Kelkar, A. A.; Patil, N. M.; Chaudhari, R. V. Tetrahedron Lett. 2002, 58, 7943. (f) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581. (g) Clement, J. B.; Hayes, J. F.; Sheldrake, H. M.; Sheldrake, P. W.; Wells, A. S. Synlett, 2001, 9, 1423. (h) Satoh, T.; Matsue, R.; Fujii, T.; Morikawa, S. Tetrahedron, 2001, 57, 3891.
35. For some recent examples of amination of aryl halides, see: (a) Gajare, A. S.; Toyota, K.; Yoshifuji, M.; Ozawa, F. Chem. Commun. 2004, 17, 1994. (b) Lu, Z.; Twilg, R. J.; Huang, S. D. Tetrahedron Lett. 2003, 44, 628. (c) Enguehard, C.; Allouchi, H.; Guieffer, A.; Buchwald, S. L. J. Org. Chem. 2003, 68, 4367. (d) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793. (e) Kelkar, A. A.; Patil, N. M.; Chaudhari, R. V. Tetrahedron Lett. 2002, 58, 7943. (f) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581. (g) Clement, J. B.; Hayes, J. F.; Sheldrake, H. M.; Sheldrake, P. W.; Wells, A. S. Synlett, 2001, 9, 1423. (h) Satoh, T.; Matsue, R.; Fujii, T.; Morikawa, S. Tetrahedron, 2001, 57, 3891.
36. For some recent examples of amination of aryl halides, see: (a) Gajare, A. S.; Toyota, K.; Yoshifuji, M.; Ozawa, F. Chem. Commun. 2004, 17, 1994. (b) Lu, Z.; Twilg, R. J.; Huang, S. D. Tetrahedron Lett. 2003, 44, 628. (c) Enguehard, C.; Allouchi, H.; Guieffer, A.; Buchwald, S. L. J. Org. Chem. 2003, 68, 4367. (d) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793. (e) Kelkar, A. A.; Patil, N. M.; Chaudhari, R. V. Tetrahedron Lett. 2002, 58, 7943. (f) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581. (g) Clement, J. B.; Hayes, J. F.; Sheldrake, H. M.; Sheldrake, P. W.; Wells, A. S. Synlett, 2001, 9, 1423. (h) Satoh, T.; Matsue, R.; Fujii, T.; Morikawa, S. Tetrahedron, 2001, 57, 3891.
37. For some recent examples of amination of aryl halides, see: (a) Gajare, A. S.; Toyota, K.; Yoshifuji, M.; Ozawa, F. Chem. Commun. 2004, 17, 1994. (b) Lu, Z.; Twilg, R. J.; Huang, S. D. Tetrahedron Lett. 2003, 44, 628. (c) Enguehard, C.; Allouchi, H.; Guieffer, A.; Buchwald, S. L. J. Org. Chem. 2003, 68, 4367. (d) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793. (e) Kelkar, A. A.; Patil, N. M.; Chaudhari, R. V. Tetrahedron Lett. 2002, 58, 7943. (f) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581. (g) Clement, J. B.; Hayes, J. F.; Sheldrake, H. M.; Sheldrake, P. W.; Wells, A. S. Synlett, 2001, 9, 1423. (h) Satoh, T.; Matsue, R.; Fujii, T.; Morikawa, S. Tetrahedron, 2001, 57, 3891.
38. For some recent examples of amination of aryl halides, see: (a) Gajare, A. S.; Toyota, K.; Yoshifuji, M.; Ozawa, F. Chem. Commun. 2004, 17, 1994. (b) Lu, Z.; Twilg, R. J.; Huang, S. D. Tetrahedron Lett. 2003, 44, 628. (c) Enguehard, C.; Allouchi, H.; Guieffer, A.; Buchwald, S. L. J. Org. Chem. 2003, 68, 4367. (d) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793. (e) Kelkar, A. A.; Patil, N. M.; Chaudhari, R. V. Tetrahedron Lett. 2002, 58, 7943. (f) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581. (g) Clement, J. B.; Hayes, J. F.; Sheldrake, H. M.; Sheldrake, P. W.; Wells, A. S. Synlett, 2001, 9, 1423. (h) Satoh, T.; Matsue, R.; Fujii, T.; Morikawa, S. Tetrahedron, 2001, 57, 3891.
39. Sasaki, M.; Dalili, S.; Yudin, A. K. J. Org. Chem. 2003, 68, 2045.
40. Kerins, F.; O'Shea, D. F. J. Org. Chem. 2002, 67, 4968.
41. Gaebert, C.; Mattay, J. Tetrahedron 1997, 53, 14297.
42. For [1,5] hydrogen shifts in C-vinyl aziridines, see: Åhman, J.; Somfai, P. Tetrahedron 1999, 55, 11595.