α-Pyridylation of chiral amines via urea coupling, lithiation and rearrangement

Organic Letters

Volumn 10, Issue 16, 2008, Pages 3567-3570

  Clayden, Jonathan ^a   Hennecke, Ulrich ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; LITHIUM; PALLADIUM; PYRIDINE DERIVATIVE; UREA;

ARTICLE; CATALYSIS; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS;

AMINES; CATALYSIS; LITHIUM; MOLECULAR CONFORMATION; PALLADIUM; PYRIDINES; STEREOISOMERISM; UREA;

EID: 54049130906     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801332n     Document Type: Article

References (50)

1. (a) Ullrich, T.; Krich, S.; Mereiter, K.; Andersen, D. J.; Meyer, M. D.; Pyerin, M. J. Med. Chem. 2002, 45, 4047.
2. (b) Lawson, E. C.; Hoekstra, W. J.; Addo, M. F.; Andrade-Gordon, P.; Damiano, B. P.; Kauffraan, J. A.; Mitchell, J. A.; Maryanoff, B. E. Bioorg. Med. Chem. Lett. 2001, 11, 2619.
3. (c) Kawata, S.; Ashzawa, S.; Hirama, M. J. Am. Chem. Soc. 1997, 119, 12012.
4. (d) Rico, J. G.; Lindmark, J. R.; Bovy, P. R. J. Org. Chem. 1993, 58, 7948.
5. (g) Aoki, M.; Ohtsuka, T.; Yamada, M.; Ohba, Y.; Yoshizaki, H.; Yasumo, H.; Sano, T.; Seto, H. J. Antibiot. 1991, 44, 582.
6. Haas, J.; Piguel, S.; Wirth, T. Org. Lett. 2002, 4, 297.
7. (b) Brunner, H.; Markus, N. Monatsh. Chem. 2002, 133, 115.
8. (c) Chelucci, G.; Pinna, G. A.; Saba, A. Tetrahedron: Asymmetry 1997, 8, 2571.
9. (d) Canary, J. W.; Allen, C. S.; Castagnetto, J. M.; Wang, Y. J. Am. Chem. Soc. 1995, 117, 8484.
10. (e) Chelucci, G.; Conti, S.; Falorni, M.; Giacomelli, G. Tetrahedron 1991, 38, 8251.
11. (f) Brunner, H.; Heinrich, F. J. Organomet. Chem. 1987, 335, 1.
12. (a) For reviews, see: Chelucci, G. Tetrahedron: Asymmetry 2005, 16, 2353.
13. Ueinishi, J.; Aburatani, S. Yuki Gosei Kagaku Kyokaishi 2007, 65, 127.
14. (b) Davies, F. A.; Szewczyk, J. M.; Reddy, R. E. J. Org. Chem. 1996, 61, 2222.
15. Kuduk, S. D.; DiPardo, R. M.; Chang, R. K.; Ng, C.; Bock, M. G. Tetrahedron Lett. 2004, 45, 6641.
16. Tang, T. P.; Ellman, J. A. J. Org. Chem. 2002, 67, 7819.
17. Alvaro, G.; Boga, C.; Savoia, D.; Umani-Ronchi, A. J. Chem. Soc., Perkin Trans. 1 1996, 875.
18. Fiore, K.; Martelli, G.; Monari, M.; Savoia, D. Tetrahedron: Asymmetry 1999, 10, 4803.
19. Deloisy, S.; Tietgen, H.; Kunz, H. Collect. Czech. Chem. Commun. 2000, 65, 816.
20. Kunz, H.; Pfrengle, W. J. Org. Chem. 1989, 54, 4261.
21. Knauer, S.; Kunz, H. Tetrahedron: Asymmetry 2005, 16, 529.
22. Loh, T.-P.; Zhou, J.-R.; Li, X.-R.; Sim, K.-Y. Tetrahedron Lett. 1999, 40, 7847.
23. Uenishi, J; Hamada, M.; Aburatani, S.; Matsui, K.; Yonemitsu, O.; Tsukube, H. J. Org. Chem. 2004, 69, 6781.
24. (e) Bull, S. D.; Davies, S. G.; Fox, D. J.; Gianotti, M.; Kelly, P. M.; Pierres, C.; Savory, E. D.; Smith, A. D. J. Chem. Soc., Perkin Trans. 1 2002, 1858.
25. (f) Campos, K. R.; Klapars, A.; Waldman, J. H.; Dormer, P. G.; Chen, C.-y. J. Am. Chem. Soc. 2005, 128, 3538.
26. Prat, L.; Dupas, G.; Duflos, J.; Quéguiner, G.; Bourguignon, J.; Levacher, V. Tetrahedron Lett. 2001, 42, 4515.
27. (g) Falorni, M.; Chelucci, G.; Conti, S.; Giacomelli, G. Synthesis 1992, 972.
28. Cossu, S.; Conti, S.; Giacomelli, G.; Falorni, M. Synthesis 1994, 1429.
29. Chelucci, G.; Cabras, M. A.; Saba, A. Tetrahedron: Asymmetry 1994, 5, 1973.
30. For an isolated example, see: Shaw, A. W.; deSolms. S. J. Tetrahedron Lett. 2001, 42, 7173.
31. Clayden, J.; Dufour, J.; Grainger, D.; Helliwell, M. J. Am. Chem. Soc. 2007, 129, 7488.
32. Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852.
33. Sergeev, A. G.; Artamkina, G. A.; Beletskaya, I. Tetrahedron Lett. 2003, 44, 4719.
34. Sergeev, A. G.; Artamkina, G. A.; Beletskaya, I. P. Russ. J. Org. Chem. 2003, 39, 1741.
35. For other urea arylations, see. Yin, J.; Buchwald, S. L. Org. Lett. 2000, 2, 1101.
36. Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043.
37. Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653.
38. Nandakumar, M. V. Tetrahedron Lett. 2004, 45, 1989.
39. Popkin, M. E.; Bellingham, R. K.; Hayes, J. F. Synlett 2006, 2716.
40. Enguehard-Gueiffier, C.; Therry, I.; Gueiffier, A.; Buchwald, S. L. Tetrahedron 2006, 62, 6042.
41. Hosseinzadeh, R.; Sarrafi, Y.; Mohadjerani, M.; Mohammadpourmir, F. Tetrahedron Lett. 2008, 49, 840.
42. Lee, C.-C.; Wang, P.-S.; Viswanath, M. B.; Leung, M.-k. Synthesis 2008, 1359.
43. For a related discussion, see: Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 2007, 129, 7734.
44. Clayden, J.; Dufour, J. Tetrahedron Lett. 2006, 47, 6945.
45. Clayden, J. Organolithiums: Selectivity for Synthesis; Pergamon: Oxford, 2002; pp 169-213.
46. Clayden, J.; Knowles, F. E.; Menet, C. J. Synlett 2003, 1701.
47. For the reasons put forward by Gawley (Gawley, R. E. J. Org. Chem. 2006, 71, 2411), we prefer the term "enantiomeric ratio" to "enantiomeric excess".
48. The difficulty of attacking an aromatic ring para to a methoxy group with an organolithium is noted in ref 11.
49. Clayden, J.; Hamilton, S. D.; Mohammed, R. T. Org. Lett. 2005, 7, 3673.
50. Arnott, G.; Clayden, J.; Hamilton, S. D. Org. Lett. 2006, 8, 5325.