Cyclocarbopalladation of alkynes: A stereoselective method for preparing dibenzoxapine containing tetrasubstituted exocyclic alkenes

Organic Letters

Volumn 8, Issue 8, 2006, Pages 1685-1688

  Yu, Hannah ^a   Richey, Rachel N ^a   Carson, Matthew W ^a   Coghlan, Michael J ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKYNE; BENZOXEPIN DERIVATIVE; PALLADIUM;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; SYNTHESIS;

ALKENES; ALKYNES; BENZOXEPINS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; MOLECULAR STRUCTURE; PALLADIUM;

EID: 33646455863     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060289a     Document Type: Article

References (40)

1. Coghlan, M. J.; Green, J. E.; Grese, T. A.; Jadhav, P. K.; Matthews, D. P.; Steinberg, M. I.; Fales, K. R.; Bell, M. G. WO 2004/052847 A2, 2004.
2. For a review of Wittig olefination, see: Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
3. (a) Simon, C.; Hosztafi, S.; Makleit, S. J. Heterocycl. Chem. 1997, 34, 349.
4. (b) Hughes, D. L. Org. Prep. Proced. Int. 1996, 28, 127.
5. (c) Mitsunobu, O. Synthesis 1981, 1.
6. (a) Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566.
7. (b) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467.
8. For reviews see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841.
9. (b) Negishi, E. Acc. Chem. Res. 1987, 20, 65.
10. (c) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, 1991; Vol. 4, p 865.
11. (d) Marek, L.; Normant, J. F. In Carbometallation Reactions in Metal Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P., Eds.; Wiley VCH: New York, 1998; pp 271-337.
12. (e) Fallis, A. G.; Forgione, P. Tetrahedron 2001, 5899.
13. (f) Mitchell, D.; Yu, H. Curr. Opin. Drug Discovery Dev. 2003, 6, 876.
14. For representative examples, see: (a) Zhang, Y.; Negishi, E. J. Am. Chem. Soc. 1989, 111, 3454.
15. (b) Burns, B.; Grigg, R.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron Lett. 1989, 30, 1135.
16. (c) Grigg, R.; Sandano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton, P. M.; Wilson, D. Tetrahedron 1997, 53, 11803.
17. (d) Poli, G.; Giambastiani, G.; Heumann, A. Tetrahedron 2000, 56, 5959.
18. (e) Frewell, P.; Grigg, R.; Sansano, J. M.; Sridharan, V.; Sukirthalingam, S.; Wilson, D.; Redpath, J. Tetrahedron 2000, 56, 7525.
19. (f) Salem, B.; Klotz, P.; Suffert, J. Org. Lett. 2003, 5, 845.
20. For selective references of seven-membered ring formation through the palladium-catalyzed cascade reaction, see: (a) References 6a and 6d.
21. (b) Grigg, R.; Savic, V.; Sridharan, V.; Terrier, C. Tetrahedron 2002, 58, 8613.
22. ( 8) For reviews, see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
23. (b) Suzuki, A. In Metal-Catalyzed Cross-Coupling Reaction; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; pp 49-97.
24. (a) Miyaura, N.; Suzuki, A. Main Group Met. Chem. 1987, 10, 295.
25. (b) Parrish, J. P.; Jung, Y. C.; Floyd, R. J.; Jung, K. W. Tetrahedron Lett. 2002, 43, 7899.
26. (c) Lei, A.; Zhang, X. Org. Lett. 2002, 4, 2285.
27. (d) Yoshida, H.; Yamaryo, Y.; Ohshita, J.; Kunai, A. Tetrahedron Lett. 2003, 44, 1541.
28. (a) Wu, G.; Rheingold, A. L.; Geig, S. L.; Heck, R. F. Organometallics 1987, 6, 1941.
29. (b) Reddy, K.; Rajender, S. K.; Lee, G. H.; Peng, S. M.; Liu, S. T. Organometallics 2001, 20, 5557.
30. Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
31. After the completion of this work, Larock et al. reported the synthesis of tetrasubstituted olefins through an intermolecular carbopalladation process. Water as cosolvent and ligandless conditions were also proved to be critical, see: (a) Zhou, C. Z.; Larock, R. C. J. Org. Chem. 2005, 70, 3765.
32. (b) Zhou, C.; Larock, R. C. Org. Lett. 2005, 7, 259.
33. (c) Zhang, X.; Larock, R. C. Org. Lett. 2003, 5, 2993.
34. (d) Zhou, C.; Emrich, D. E.; Larock, R. C. Org. Lett. 2003, 5, 1579.
35. 3 under the optimized conditions. They all afforded good 2a/6 selectivity, but the yield is generally lower.
36. Watanabe, T.; Miyaura, N.; Suzuki, A. Synlett 1992, 207.
37. It was necessary to convert 2b to final target 1b soon after isolation. 2b could undergo a light-catalyzed isomerization during storage.
38. (a) Cacchi, S. J. Organomet. Chem. 1999, 576, 42.
39. (b) Larock, R. C. J. Organomet. Chem. 1999, 576, 111.
40. (c) Roesch, K. R.; Zhang, H.; Larock, R. C. J. Org. Chem. 2001, 66, 8042.