Stereospecific intramolecular C-H amination of 1-aza-2-azoniaallene salts

Journal of the American Chemical Society

Volumn 134, Issue 24, 2012, Pages 9890-9893

  Bercovici, Daniel A ^a   Brewer, Matthias ^a  

^a UNIVERSITY OF VERMONT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION REACTION; BENZYLIC; CHIRAL CENTERS; COMPETITION REACTIONS; ELECTRON-DEFICIENT; ELECTRON-RICH; ENANTIOMERIC EXCESS; INSERTION MECHANISM; INTRAMOLECULAR AMINATION; LEWIS ACID; PYRAZOLINES; STEREOSPECIFIC;

SALTS;

AMINES;

1 AZA 2 AZONIAALLENE; CARBON; HYDROGEN; LEWIS ACID; PYRAZOLE; PYRAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; ELECTRON; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION;

EID: 84862517858     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja303054c     Document Type: Article

References (57)

1. For selected recent reviews see: Themed issue on "C-H functionalisation in organic synthesis", Chem. Soc. Rev. 2011, 40 (4), 1845-2040.
2. Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417
3. Breslow, R.; Gellman, S. H. J. Chem. Soc., Chem. Commun. 1982, 1400
4. Breslow, R.; Gellman, S. H. J. Am. Chem. Soc. 1983, 105, 6728
5. Du Bois, J. Org. Process Res. Dev. 2011, 15, 758
6. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
7. Dick, A. R.; Sanford, M. S. Tetrahedron 2006, 62, 2439
8. Sun, K.; Sachwani, R.; Richert, K. J.; Driver, T. G. Org. Lett. 2009, 11, 3598
9. Nägeli, I.; Baud, C.; Bernardinelli, G.; Jacquier, Y.; Moraon, M.; Müllet, P. Helv. Chim. Acta 1997, 80, 1087
10. Ghose, A. K.; Viswanadhan, V. N.; Wendoloski, J. J. J. Comb. Chem. 1999, 1, 55
11. Lesney, M. S. Todays Chemist at Work 2004, 26
12. Bur, S. K.; Padwa, A. Chem. Rev. 2004, 104, 2401
13. Yu, X.-Q.; Huang, J.-S.; Zhou, X.-G.; Che, C.-M. Org. Lett. 2000, 2, 2233
14. Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed. 2001, 40, 598
15. Hinman, A.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 11510
16. Fleming, J. J.; Du Bois, J. J. Am. Chem. Soc. 2006, 128, 3926
17. Collet, F.; Lescot, C.; Dauban, P. Chem. Soc. Rev. 2011, 40, 1926
18. Liang, C.; Robert-Peillard, F.; Fruit, C.; Müller, P.; Dodd, R. H.; Dauban, P. Angew. Chem., Int. Ed. 2006, 45, 4641
19. Reddy, R. P.; Davies, H. M. L. Org. Lett. 2006, 8, 5013
20. Liang, C.; Collet, F.; Robert-Peillard, F.; Müller, P.; Dodd, R. H.; Dauban, P. J. Am. Chem. Soc. 2008, 130, 343
21. Wang, Q. R.; Jochims, J. C.; Kohlbrandt, S.; Dahlenburg, L.; Altalib, M.; Hamed, A.; Ismail, A. E. H. Synthesis 1992, 710
22. Javed, M. I.; Wyman, J. M.; Brewer, M. Org. Lett. 2009, 11, 2189
23. Wyman, J.; Javed, M. I.; Al-Bataineh, N.; Brewer, M. J. Org. Chem. 2010, 75, 8078
24. Wang, Q. R.; Amer, A.; Mohr, S.; Ertel, E.; Jochims, J. C. Tetrahedron 1993, 49, 9973
25. Wirschun, W. G.; Al-Soud, Y. A.; Nusser, K. A.; Orama, O.; Maier, G. M.; Jochims, J. C. J. Chem. Soc., Perkin Trans. 1 2000, 4356
26. Wyman, J. M.; Jochum, S.; Brewer, M. Synth. Commun. 2008, 38, 3623
27. Mundal, D. A.; Lutz, K. E.; Thomson, R. J. Org. Lett. 2009, 11, 465
28. Mundal, D. A.; Avetta, C. T.; Thomson, R. J. Nat. Chem. 2010, 2, 294
29. Gladstone, W. A. F.; Norman, R. O. C. J. Chem. Soc. 1965, 3048
30. Gladstone, W. A. F.; Norman, R. O. C. J. Chem. Soc. C 1966, 1527 and ref 21
31. Léavai, A. J. Heterocycl. Chem. 2002, 39, 1
32. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863
33. Patil, N. T.; Singh, V. Chem. Commun. 2011, 47, 11116
34. Dang, T.-T.; Abdellah, I.; Canac, Y.; Chauvin, R. ChemCatChem 2011, 3, 1491
35. Cui, S.-L.; Wang, J.; Wang, Y.-G. Org. Lett. 2007, 10, 13
36. Alex, K.; Tillack, A.; Schwarz, N.; Beller, M. Org. Lett. 2008, 10, 2377
37. Waldo, J. P.; Mehta, S.; Larock, R. C. J. Org. Chem. 2008, 73, 6666
38. Ju, Y.; Varma, R. S. J. Org. Chem. 2005, 71, 135
39. Grimm, J. B.; Wilson, K. J.; Witter, D. J. J. Org. Chem. 2009, 74, 6390
40. Manyem, S.; Sibi, M. P.; Lushington, G. H.; Neuenswander, B.; Schoenen, F.; Aubé, J. J. Comb. Chem. 2006, 9, 20
41. Morkovnik, A. S.; Okhlobystin, O. Y. Chem. Heterocycl. Compd. 1985, 21, 461
42. Fiori, K. W.; Espino, C. G.; Brodsky, B. H.; Du Bois, J. Tetrahedron 2009, 65, 3042
43. Wei, M. J.; Fang, D. C.; Liu, R. Z. J. Org. Chem. 2002, 67, 7432
44. Borodkin, G. I.; Shubin, V. G. Russ. Chem. Rev. 2008, 77, 395
45. Kikugawa, Y. Heterocycles 2009, 78, 571
46. Falvey, D. E. Nitrenium Ions. In Reactive Intermediate Chemistry; Moss, R. A.; Platz, M. A.; Jones, M., Eds.; John Wiley & Sons, Inc.: Hoboken, NJ, 2004; p 593.
47. Kennedy, S. A.; Novak, M.; Kolb, B. A. J. Am. Chem. Soc. 1997, 119, 7654
48. Bosold, F.; Boche, G. Angew. Chem., Int. Ed. Engl. 1990, 29, 63
49. Miller, J. A. Cancer Res. 1970, 30, 559
50. Vedejs, E.; Sano, H. Tetrahedron Lett. 1992, 33, 3261
51. Bowen, E. G.; Wardrop, D. J. Org. Lett. 2010, 12, 5330
52. Wardrop, D. J.; Zhang, W.; Landrie, C. L. Tetrahedron Lett. 2004, 45, 4229
53. Rudchenko, V. F.; Ignatov, S. M.; Kostyanovsky, R. G. J. Chem. Soc., Chem. Commun. 1990, 261
54. McIlroy, S.; Moran, R. J.; Falvey, D. E. J. Phys. Chem. A 2000, 104, 11154
55. Falvey, D. E. J. Phys. Org. Chem. 1999, 12, 589
56. Nishiyama, H.; Arai, H.; Kanai, Y.; Kawashima, H.; Itoh, K. Tetrahedron Lett. 1986, 27, 361
57. 5,5-Disubstituted pyrazolines have been reported to be particularly unstable and decompose via oxidation: Cox, C. D.; Breslin, M. J.; Mariano, B. J. Tetrahedron Lett. 2004, 45, 1489