Palladium(0)-catalyzed stereoselective cyclization of allenenes: Divergent synthesis of pyrrolidines and 3-azabicyclo[3.1.0]hexanes from single allenenes

Journal of Organic Chemistry

Volumn 69, Issue 13, 2004, Pages 4541-4544

  Ohno, Hiroaki ^a   Takeoka, Yusuke ^a   Kadoh, Yoichi ^a   Miyamura, Kumiko ^a   Tanaka, Tetsuaki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYST ACTIVITY; PALLADIUM; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ALLENENES; STEREOSELECTIVE CYCLIZATION;

AROMATIC COMPOUNDS;

3 AZABICYLCO[3.1.0]HEXANE DERIVATIVE; ALLENE DERIVATIVE; ALLENENE DERIVATIVE; CYCLOHEXANE DERIVATIVE; PALLADIUM; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 3042704606     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049663f     Document Type: Article

References (37)

1. For recent reviews, see: (a) Zimmer, R.; Dinesh, C. U.; Nandanan, E.; Khan, F. A. Chem. Rev. 2000, 100, 3067-3125.
2. (b) Hashmi, A. S. K. Angew. Chem., Int. Ed. 2000, 39, 3590-3593.
3. For pioneering works, see: (a) Larock, R. C.; Berrios-Peña, N. G.; Fried, C. A. J. Org. Chem. 1991, 56, 2615-2617.
4. (b) Davies, I. W.; Scopes, D. I. C.; Gallagher, T. Synlett 1993, 85.
5. For a recent review, see: (c) Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12-21.
6. For some recent examples, see: (a) Ohno, H.; Toda, A.; Miwa, Y.; Taga, T.; Osawa, E.; Yamaoka, Y.; Fujii, N.; Ibuka, T. J. Org. Chem. 1999, 64, 2992-2993.
7. (b) Ma, S.; Zhao, S. J. Am. Chem. Soc. 1999, 121, 7943-7944.
8. (c) Kang, S. K.; Kim, K.-J. Org. Lett. 2001, 3, 511-514.
9. (d) Ohno, H.; Anzai, M.; Toda, A.; Ohishi, S.; Fujii, N.; Tanaka, T.; Takemoto, Y.; Ibuka, T. J. Org. Chem. 2001, 66, 4904-4914.
10. (e) Ohno, H. Yakugaku Zasshi 2001, 121, 733-741.
11. (f) Hiroi, K.; Hiratsuka, Y.; Watanabe, K.; Abe, I.; Kato, F.; Hiroi, M. Tetrahedron: Asymmetry 2002, 13, 1351-1353.
12. Kang, S.-K.; Baik, T.-G.; Kulak, A. N.; Ha, Y.-H.; Lim, Y.; Park, J. J. Am. Chem. Soc. 2000, 122, 11529-11530.
13. Shin, S.; RajanBabu, T. V. J. Am. Chem. Soc. 2001, 123, 8416-8417.
14. (a) Löfstedt, J.; Franzén, J.; Bäckvall, J.-E. J. Org. Chem. 2001, 66, 8015-8025.
15. (b) Franzén, J.; Löfstedt, J.; Dorange, I.; Bäckvall, J.-E. J. Am. Chem. Soc. 2002, 124, 11246-11247.
16. (c) Franzén, J.; Bäckvall, J.-E. J. Am. Chem. Soc. 2003, 125, 6056-6057.
17. (a) Brummond, K. M.; Wan, H.; Kent, J. L. J. Org. Chem. 1998, 63, 6535-6545.
18. (b) Mukai, C.; Nomura, I.; Yamanishi, K.; Hanaoka, M. Org. Lett. 2002, 4, 1755-1758.
19. (a) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844.
20. (b) Makino, T.; Itoh, K. J. Org. Chem. 2004, 69, 395-405 and references therein.
21. For preliminary communications, see: (a) Ohno, H.; Miyamura, K.; Takeoka, Y.; Tanaka, T. Angew. Chem., Int. Ed. 2003, 42, 2647-2650.
22. (b) Ohno, H.; Takeoka, Y.; Miyamura, K.; Kadoh, Y.; Tanaka, T. Org. Lett. 2003, 5, 4763-4766.
23. (a) Ohno, H.; Toda, A.; Oishi, S.; Tanaka, T.; Takemoto, Y.; Fujii, N.; Ibuka, T. Tetrahedron Lett. 2000, 41, 5131-5134.
24. (b) Ohno, H.; Miyamura, K.; Tanaka, T.; Oishi, S.; Toda, A.; Takemoto, Y.; Fujii, N.; Ibuka, T. J. Org. Chem. 2002, 67, 1359-1367.
25. (a) Claesson, A.; Olsson, L.-I. J. Am. Chem. Soc. 1979, 101, 7302-7311.
26. See also, (b) Borden, W. T.; Corey, E. J. Tetrahedron Lett. 1969, 10, 313-316.
27. Myers, A. G.; Zheng, B. J. Am. Chem. Soc. 1996, 118, 4492-4493.
28. Searles, S.; Li, Y.; Nassim, B.; Lopes, M.-T. R.; Tran, P. T.; Crabbé, P. J. Chem. Soc., Perkin Trans. 1 1984, 747-751.
29. Similarly, the reaction of 17d with sterically congested 2-iodotoluene gave a mixture of unidentified products, and the desired arylated pyrrolidine was not isolated.
30. The reaction of the unsubstituted allenene led to a complex mixture of unidentified products.
31. (a) Ohno, H.; Toda, A.; Miwa, Y.; Taga, T.; Fujii, N.; Ibuka, T. Tetrahedron Lett. 1999, 40, 349-352.
32. (b) Ohno, H.; Toda, A.; Fujii, N.; Takemoto, Y.; Tanaka, T.; Ibuka, T. Tetrahedron 2000, 56, 2811-2820.
33. For preparation of 2-ethynylaziridines, see: (c) Ohno, H.; Toda, A.; Fujii, N.; Ibuka, T. Tetrahedron: Asymmetry 1998, 9, 3929-3933.
34. (d) Ohno, H.; Toda, A.; Takemoto, Y.; Fujii, N.; Ibuka, T. J. Chem. Soc., Perkin Trans. 1 1999, 2949-2962.
35. Decreased loading of the allyl carbonate (2 equiv) lowered the yields. It is presumably due to the side reaction of allylpalladium(II) intermediate with another molecule of the allyl carbonate.
36. Ma, S.; Jiao, N.; Zhao, S.; Hou, J. J. Org. Chem. 2002, 67, 2837-2847.
37. 3CN in the presence of NaOMe. However, unchanged starting allenene 17d was recovered in both cases. The reaction in AcOH using the Oppolzer's conditions afforded unidentified products and no cyclopropane was obtained.