Synthesis of 2,6-disubstituted piperazines by a diastereoselective palladium-catalyzed hydroamination reaction

Organic Letters

Volumn 10, Issue 2, 2008, Pages 329-332

  Cochran, Brian M ^a   Michael, Forrest E ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; PIPERAZINE DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMINATION; CATALYSIS; MOLECULAR STRUCTURE; PALLADIUM; PIPERAZINES; STEREOISOMERISM;

EID: 38749153968     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702891p     Document Type: Article

References (27)

1. Ward, S. E.; Harrington, F. P.; Gordon, L. J.; Hopley, S. C.; Scott, C. M.; Watson, J. M. J. Med. Chem. 2005, 48, 3478-3480.
2. Leopoldo, M.; Lacivita, E.; Colabufo, N. A.; Contino, M.; Berardi, F.; Perrone, R. J. Med. Chem. 2005, 48, 7919-7922.
3. Bruncko, M.; Oost, T. K.; Belli, B. A.; Ding, H.; Joseph, M. K.; Kunzer, A.; Martineau, D.; McClellan, W. J.; Mitten, M.; Ng, S.-C.; Nimmer, P. M.; Oltersdorf, R.; Park, C.-M.; Petras, A. M.; Shoemaker, A. R.; Song, X.; Wang, X.; Wendt, M. D.; Zhang, H.; Fesik, S. W.; Rosenberg, S. H.; Elmore, S. W. J. Med. Chem. 2007, 50, 641-662.
4. Bombrun, A.; Gerber, P.; Casi, G.; Terradillos, O.; Antonsson, B.; Halazy. J. Med. Chem. 2003, 46, 4365-4368.
5. Jacobsen, E. J.; Stelzer, L. S.; TenBrink, R. E.; Belonga, K. L.; Carter, D. B.; Im, H. K.; Im, W. B.; Sethy, V. H.; Tang, A. H.; VonVoigtlander, P. F.; Petke, J. D.; Zhong, W.-Z.; Mickelson, J. W. J. Med. Chem. 1999, 42, 1123-1144.
6. Askin, D.; Eng, K. K.; Rossen, K.; Purick, R. M.; Weiss, K. M.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1994, 35, 673-676.
7. For a review on diketopiperazine synthesis, see: Dinsmore, C. J.; Beshore, D. C. Tetrahedron 2002, 58, 3297-3312.
8. Method for the synthesis of achiral 2,6-disubstituted piperazines: Cignarella, G.; Gallo, G. G. J. Heterocycl. Chem. 1974, 11, 985-989.
9. Mickelson, J. W.; Belonga, K. L.; Jacobsen, E. J. J. Org. Chem. 1995, 60, 417-4183.
10. Schanen, V.; Cherrier, M.-P.; de Melo, S. J.; Quirion, J.-C.; Husson, H.-P. Synthesis 1996, 7, 833-837.
11. Nakhla, J. S.; Wolfe, J. P. Org. Lett. 2007, 9, 3279-3282.
12. Michael, F. E.; Cochran, B. M. J. Am. Chem. Soc. 2006, 128, 4246-4247.
13. Basha, F. Z.; DeBernardis, J. F. J. Heterocycl. Chem. 1987, 24, 789-791.
14. Cochran, B. M.; Michael, F. E. J. Am. Chem. Soc. 2008. In press.
15. (a) Piper, J. R.; Stringfellow, C. R., Jr.; Johnston, T. P. J. Med. Chem. 1966, 9, 911-920.
16. (b) Kano, S.; Yokomatsu, T.; Iwasawa, H.; Shibuya, S. Heterocycles 1987, 26, 2805-2809.
17. (c) Han, M. S.; Oh, D. J.; Kim, D. H. Bioorg. Med. Chem. Lett. 2004, 14, 701-705.
18. The amino alcohols were derived from enantiopure amino acids by methods described in ref 15.
19. Posakony, J. J.; Grierson, J. R.; Tewson, T. J. J. Org. Chem. 2002, 67, 5164-5169.
20. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994; p 689.
21. (a) Hoffmann, R. W. Chem. Rev. 1989, 89, 1841-1860.
22. (b) Johnson, F. Chem. Rev. 1968, 68, 375-413.
23. For an example of a 2,5-disubstituted piperazine boat, see: Tsuboyama, K.; Uzawa, J.; Koda, R.; Mitsunori, N.; Kobayashi, K.; Sakurai, T. Tetrahedron Lett. 1977, 18, 2895-2898.
24. 1H coupling constants. See Supporting Information for a detailed analysis of compound 10d.
25. Corey, E. J.; Feiner, N. F. J. Org. Chem. 1980, 45, 765-780.
26. (a) Hong, S.; Marks, T. Acc. Chem. Res. 2004, 37, 673-686.
27. (b) Kim, Y. K.; Livinghouse, T.; Horino, Y. J. Am. Chem. Soc. 2003, 125, 9560-9561.