Cyclocarboamination of alkynes with aziridines: Synthesis of 2,3-dihydropyrroles by a catalyzed formal [3 + 2] cycloaddition

Journal of the American Chemical Society

Volumn 131, Issue 22, 2009, Pages 7528-7529

  Wender, Paul A ^a   Strand, Daniel ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINES; BRONSTED ACIDS; CATALYST LOADINGS; CHEMICAL EQUATIONS; MILD REACTION CONDITIONS; REGIO-SELECTIVE;

CHEMICAL REACTIONS;

ACETYLENE;

2,3 DIHYDROPYRROLE; ALKYNE DERIVATIVE; AZIRIDINE DERIVATIVE; CARBON; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG; ALKYNE;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOADDITION; CHEMISTRY; SYNTHESIS;

ALKYNES; AZIRIDINES; CATALYSIS; CYCLIZATION; PYRROLES;

EID: 67650552631     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja901799s     Document Type: Article

References (41)

1. Wender, P. A.; Verma, V. A.; Paxton, T. J.; Pillow, T. H. Acc. Chem. Res. 2008, 41, 40.
2. (a) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720.
3. (b) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876.
4. (c) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Pham, S. M.; Zhang, L. J. Am. Chem. Soc. 2005, 127, 2836.
5. (a) Alper, H.; Urso, F. J. Am. Chem. Soc. 1983, 105, 6731.
6. (b) Calet, S.; Urso, F.; Alper, H. J. Am. Chem. Soc. 1989, 111, 931.
7. (c) Ardura, D.; Lopez, R.; Sordo, T. S. J. Org. Chem. 2006, 71, 7315.
8. For related Pd studies, see: (d) Ney, J. E.; Wolfe, J. P. J. Am. Chem. Soc. 2006, 128, 15415.
9. (a) Bellina, F.; Rossi, R. Tetrahedron 2006, 62, 7213.
10. (b) Cox, C. D.; et al. J. Med. Chem. 2008, 51, 4239.
11. (c) Smela, E. Adv. Mater. 2003, 15, 481.
12. Kinderman, S. S.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. J. T. Org. Lett. 2001, 3, 2045.
13. Feldman, K. S.; Bruendl, M. M.; Schildknegt, K.; Bohnstedt, A. C. J. Org. Chem. 1996, 61, 5440.
14. (a) Jacoby, D.; Celerier, J. P.; Haviari, G.; Petit, H.; Lhommet, G. Synthesis 1992, 9, 884.
15. (b) Zhu, W.; Cai, G.; Ma, D. Org. Lett. 2005, 7, 5545.
16. (a) Wolf, L. B.; Tjen, K. C. M. F.; Rutjes, F. P. J. T.; Hiemstra, H.; Schoemaker, H. E. Tetrahedron Lett. 1998, 5081.
17. (b) Busacca, C. A.; Dong, Y. Tetrahedron Lett. 1996, 3947.
18. (c) Yin, Y.; Ma, W.; Chai, Z.; Zhao, G. J. Org. Chem. 2007, 5731.
19. (d) Ma, S.; Yu, F.; Li, J.; Gao, W. Chem. - Eur. J. 2007, 247.
20. Zhou, X.; Zhang, H.; Yuan, J.; Mai, L.; Li, Y. Tetrahedron Lett. 2007, 48, 7236.
21. (a) Ding, C.-H.; Dai, L.-X.; Hou, X.-L. Tetrahedron 2005, 61, 9586.
22. (b) Knight, D. W.; Redfern, A. L.; Gilmore, J. J. Chem. Soc., Perkin Trans. 1 2002, 622.
23. Sonesson, C.; Hallberg, A. Tetrahedron Lett. 1995, 36, 4505.
24. (a) Saegusa, T.; Ito, Y.; Kinoshita, H; Tomita, S. J. Org. Chem. 1971, 36, 3316.
25. (b) Schollkopf, U.; Hantke, K. Liebigs Ann. Chem. 1973, 1571.
26. (c) Guo, C.; Xue, M.-X.; Zhu, M.-K.; Gong, L.-Z Angew. Chem., Int. Ed. 2008, 47, 3414.
27. Wurz, R. P.; Charette, A. B. Org. Lett. 2005, 7, 2313.
28. Starting with an enantioenriched aziridine (67% ee), essentially racemic product was obtained which supports the notion of an achiral intermediate.
29. (a) Ungureanu, I.; Bologa, C.; Chayerm, S.; Mann, A. Tetrahedron Lett. 1999, 40, 5315.
30. (b) Ungureanu, I.; Klotz, P.; Mann, A. Angew. Chem., Int. Ed. 2000, 39, 4615.
31. (c) Nakagawa, M.; Kawahara, M. Org. Lett. 2000, 2, 953.
32. (d) Yadav, J. S.; Reddy, B. V. S.; Pandey, S. K.; Srihari, P.; Prathap, T. Tetrahedron Lett. 2001, 42, 9089.
33. (e) Bergmeier, S. C.; Katz, S. J.; Huang, J.; McPherson, H.; Donoghue, P. J.; Reed, D. D. Tetrahedron Lett. 2004, 45, 5011.
34. For reactions with azetidines see: (f) Ungureanu, I.; Klotz, P.; Schoenfelder, A.; Mann, A. Chem. Commun. 2001, 958.
35. (a) Gandhi, S.; Bisai, A.; Prasad, B. A. B.; Singh, V. K. J. Org. Chem. 2007, 72, 2133.
36. (b) Yadav, V. K.; Sriramurthy, V. J. Am. Chem. Soc. 2005, 127, 16366.
37. Hiyama, T.; Koide, H.; Fujita, S.; Nozaki, H. Tetrahedron 1973, 29, 3137.
38. Madhushaw, R. J.; Hu, C.-C.; Liu, R.-S. Org. Lett. 2002, 4, 23-4151.
39. The use of 1.5 equiv of alkyne gives 3a in 55% yield under standard conditions.
40. Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373.
41. For reactions with 1b and nitriles, see ref 16b.