Palladium-catalyzed cross-couplings of 2-tributylstannyl-N-Boc-2,3-dehydropiperidine, a cyclic enecarbamate

Letters in Organic Chemistry

Volumn 5, Issue 7, 2008, Pages 587-590

  Simas, Alessandro B C ^a   de Sales, Daniel L ^a   Cavalcante, Samir F A ^a   de Medeiros, Cristina M ^a   Moraes, Sandro H S ^a   de Carvalho, Erika M ^b  

^a FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^b INSTITUTO OSWALDO CRUZ   (Brazil)

Author keywords

Cyclic amine; Heterocycle; Piperidine; Stille coupling; Synthesis; Umpolung

Indexed keywords

EID: 57349154042     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017808785982149     Document Type: Article

References (26)

1. Laschat, S.; Dickner, T. Synthesis, 2000, 13, 1781
2. Pearson, M.S.M.; Mathé-Allainmat, M.; Fargeas, V.; Lebreton, J. Eur. J. Org. Chem., 2005, 2159.
3. Foti, C.J.; Comins, D.L. J. Org. Chem., 1995, 60, 2656
4. Nicolaou, K.C.; Shi, G.Q.; Namoto, K.; Bernal, F. Chem Comm., 1998, 1757
5. Occhiato, E.G. Mini-Rev. Org. Chem., 2004, 1, 149.
6. Luker, T.; Hiemstra, H.; Speckamp, W.N. Tetrahedron Lett., 1996, 37, 8257.
7. Occhiato, E.G.; Trabochi, A.; Guama, A. J. Org. Chem., 2001, 66, 2459.
8. Lepifte, F.; Clavier, S.; Bouyssou, P.; Coudert, G. Tetrahedron, 2001, 57, 6969.
9. Stille, J.K. Angew. Chem. Int. Ed. Eng., 1986, 25, 508.
10. Speckamp and coll, have prepared five and six-membered 2-stannylated enecarbamates by such means but their use in catalyzed cross-coupling has not been broadly explored: Luker, T.; Hiemstra, H.; Speckamp, W.N. J. Org. Chem., 1997, 62, 8131.
11. Ferrali, A.; Gurana, A.; Lo Galbo, F.; Occhiato, E.G. Tetrahedron Lett., 2004, 45, 5271.
12. Beak, P.; Lee, W.K. J. Org. Chem., 1993, 58, 1109.
13. Cossy, J.; Cases, M.; Pardo, D.G. Synth. Commun., 1997, 27, 2769. 14 Farina, V.; Krishnan, B. J. Am. Chem. Soc., 1991, 113, 9585.
14. Farina, V.; Krishnamurthy, V.; Scott, W.J. Org. React., 1997, 50, 1.
15. Marino, J.P.; Long, J.F. J. Am. Chem. Soc., 1988, 110, 7916.
16. Liebeskind, L.S.; Fengl, R.W. J. Org. Chem., 1990, 55, 5359.
17. Amatore, C.; Bahsoun, A.A.; Jutand, A.; Meyer, G.; Ntepe, A.N.; Ricard, L. J. Am. Chem. Soc., 2003, 125, 4212.
18. Espinet, P.; Echavarren, A.M. Angew. Chem. Int. Ed. Eng., 2004, 43, 4704
19. Casado, A.L.; Espinet, P. J. Am. Chem. Soc., 1998, 120, 8978.
20. For recent studies supporting the currently accepted mechanism: Santos, L.S.; Rosso, G.B.; Pilli, R.A.; Eberlin, M.N. J. Org. Chem., 2007, 72, 5809
21. Álvarez, R.; Faza, O.N.; López, C.S.; de Lera, A.R. Org. Lett., 2006, 8, 35.
22. Han, H.J.; Stoltz, B.M.; Corey, E.J. J. Am. Chem. Soc., 1999, 121, 7600.
23. Casado, A.L.; Espinet, P.; Gallego, A.M. J. Am. Chem. Soc., 2000, 122, 11771.
24. Littke, A.F.; Schwarz, L.; Fu, G.C. J. Am. Chem. Soc., 2002, 124, 6343
25. Mee, S.P.H.; Lee, V.; Baldwin, J.E. Chem. Eur. J., 2005, 11, 3294.
26. -1) 2977, 2933, 1701, 1601, 1367, 1232, 1161, 851.