Efficient aziridination of olefins catalyzed by mixed-valent dirhodium(II,III) caprolactamate

Organic Letters

Volumn 7, Issue 13, 2005, Pages 2787-2790

  Catino, Arthur J ^a   Nichols, Jason M ^a   Forslund, Raymond E ^a   Doyle, Michael P ^a  

^a Bldg 142   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AZIRIDINE DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ORGANOMETALLIC COMPOUND; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALKENES; AZIRIDINES; CATALYSIS; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; RHODIUM;

EID: 27944498664     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0510973     Document Type: Article

References (50)

1. For a general review of carbon-nitrogen bond formation, see: (a) Kemp, J. E. G. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, UK, 1991; Vol. 7, p 469.
2. Selected olefin aziridination reviews, see: (a) Müller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905.
3. (b) Dauban, P.; Dodd, R. H. Synlett 2003, 1571.
4. (c) Jacobsen, E. N. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Phaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 2, p 607.
5. (d) Müller, P. In Advances in Catalytic Processes; Doyle, M. P., Ed; JAI Press, Inc.: Greenwich, 1997; Vol. 2, p 113.
6. For a comprehensive review of aziridine ring opening, see: (a) Hu, X. E. Tetrahedron 2004, 60, 2701.
7. Selected recent synthesis of aziridines via nitrenes: (a) Dauban, P.; Saniére, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707.
8. (b) Duran, F.; Leman, L.; Ghini, A.; Burton, G.; Dauban, P.; Dodd, R. H. Org. Lett. 2002, 4, 2481.
9. (c) Siu, T.; Yudin, A. K. J. Am. Chem. Soc. 2002, 124, 530.
10. Selected enantioselective aziridinations, see: (a) Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326.
11. (b) Evans, D. A.; Bilodeau, M. T.; Faul, M. M. J. Am. Chem. Soc. 1994, 116, 2742.
12. (c) Sanders, C. J.; Gillespie, K. M.; Bell, D.; Scott, P. J. Am. Chem. Soc. 2000, 122, 7132.
13. (d) Liang, J.-L.; Huang, J.-S.; Yu, X.-Q.; Zhu, N.; Che, C.-M. Chem. Eur. J. 2002, 8, 1563.
14. 4+-catalyzed aziridination, see: (a) Müller, P.; Baud, C.; Jacquier, Y. Tetrahedron 1996, 52, 1543.
15. (b) Müller, P.; Baud, C.; Jacquier, Y. Can. J. Chem. 1998, 76, 738.
16. (c) Guthikonda, K.; DuBois, J. J. Am. Chem. Soc. 2002, 124, 13672.
17. (d) Liang, J.-L.; Yuan, S.-X.; Chan, P. W. H.; Che, C.-M. Org. Lett. 2002, 4, 4507.
18. (e) Liang, J. L.; Yuan, S. X.; Chan, P. W. H.; Che, C. M. Tetrahedron Lett. 2003, 44, 5917.
19. (f) Fruit, C.; Müller, P. Tetrahedron: Asymmetry 2004, 15, 1019.
20. Catino, A. J.; Forslund, R. E.; Doyle, M. P. J. Am. Chem. Soc. 2004, 126, 13622.
21. + < 1 kcal/mol: Doyle, M. P.; Ren, T. Progress in Inorganic Chemistry; Karlin, K., Ed; Wiley: New York, 2001; Vol. 49, p 113.
22. (a) Cotton, F. A.; Walton, R. A. Multiple Bonds Between Metal Atoms; Wiley: New York, 1982; p 390.
23. (b) Cotton, F. A.; Walton, R. A. Multiple Bonds Between Metal Atoms, 2nd ed.; Oxford: New York, 1993; p 475.
24. See Supporting Information for X-ray crystal data.
25. 5+ halide complexes containing N-C-N dinuclear bridging ligands, see: (a) Kadish, K. M.; Phan, T. D.; Giribabu, L.; Van Caemelbecke, E.; Bear, J. L. Inorg. Chem. 2003, 42, 8663.
26. (b) Bear, J. L.; Yao, C. L.; Liu, L. M.; Capdevielle, F. J.; Korp, J. D.; Albright, T. A.; Kang, S. K.; Kadish, K. M. Inorg. Chem. 1989, 28, 1254.
27. For bromine-catalyzed aziridination, see: Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844.
28. For subsequent studies by other groups, see: (a) Ali, S. I.; Nikalje, M. D.; Sudalai, A. Org. Lett. 1999, 1, 705.
29. (b) Dauban, P.; Dodd, R. H. Tetrahedron Lett. 2001, 42, 1037.
30. (c) Thakur, V. V.; Sudalai, A. Tetrahedron Lett. 2003, 44, 989.
31. (d) Jain, S. L.; Sharma, V. B.; Sain, B. Tetrahedron Lett. 2004, 45, 8731.
32. 4.
33. Thakur, V. V.; Talluri, S. K.; Sudalai, A. Org. Lett. 2003, 5, 861.
34. Electron-deficient (methyl-trans-cinnamate), trisubstituted (1-methylcyclohexene), and α,α-disubstituted (α-methylstyrene) olefins were not reactive substrates for this protocol.
35. 4 (0.0027 mmol, 0.1 mol %). To the mixture was added NBS (2.99 mmol, 110 mol %) in one portion, and the color of the solution immediately turned from light blue to red. The flask was sealed with a septum allowing inclusion of air. After 12 h, silica gel was added to the reaction mixture and the solvent was evaporated. Column chromatography yielded the analytically pure compound.
36. 2) was observed after 24 h.
37. a = 4.55: Morris, J. C.; Salazar, A. S.; Wineman, M. A. J. Am. Chem. Soc. 1948, 70, 2036.
38. Rangappa, K. S. J. Phys. Org. Chem. 2001, 14, 684.
39. Hassner, A.; Boerwinkle, F. J. Am. Chem. Soc. 1968, 90, 216.
40. Newcomb, M.; Johnson, C. C.; Manek, M. B.; Varick, T. R. J. Am. Chem. Soc. 1992, 114, 10915.
41. 2.
42. For dirhodium carboxamidates as Lewis acids, see: (a) Doyle, M. P.; Phillips, I. M.; Hu, W. H. J. Am. Chem. Soc. 2001, 123, 5366.
43. (b) Anada, M.; Washio, T.; Shimada, N.; Kitagaki, S.; Nakajima, M.; Shiro, M.; Hashimoto, S. Angew. Chem., Int. Ed. 2004, 43, 2665.
44. (c) Doyle, M. P.; Valenzuela, M.; Huang, P. L. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5391.
45. (d) Valenzuela, M.; Doyle, M. P.; Hedberg, C.; Hu, W.; Holmstrom, A. Synlett 2004, 13, 2422.
46. (e) Forslund, R. E.; Cain, J.; Colyer, J.; Doyle, M. P. Adv. Synth. Catal. 2005, 347, 87.
47. 2. It was found that 12 acts as an electrophilic source of bromine, as treatment with succinimide yields NBS and aminobromide 3 in an equilibrium mixture (see Supporting Information).
48. 4 (1 mol %, 49%).
49. 2-halides, see: Bear, J. L.; Han, B.; Wu, Z.; Van Caemelbecke, E.; Kadish, K. M. Inorg. Chem. 2001, 40, 2275.
50. 4 to give a white precipitate determined to be AgCl by its solubility in ammonium hydroxide. (Chemical Equation Presented)