A new Co2(CO)8-mediated tandem [5 + 1]/[2 + 2 + 1]-cycloaddition reaction: A one-pot synthesis of tricyclic δ-lactones from cis-epoxy ene-ynes

Journal of the American Chemical Society

Volumn 125, Issue 32, 2003, Pages 9610-9611

  Odedra, Arjan ^a   Wu, Chang Jung ^a   Madhushaw, Reniguntala J ^a   Wang, Su Lein ^a   Liu, Rai Shung ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALKYNE DERIVATIVE; BENZENE DERIVATIVE; CARBON; CYCLOHEXANE; EPOXIDE; LACTONE DERIVATIVE; NITROGEN; OXYGEN; TRANSITION ELEMENT;

ADDITION REACTION; ARTICLE; CHEMICAL BOND; CIS ISOMER; CYCLIZATION; CYCLOADDITION; NUCLEAR MAGNETIC RESONANCE; PRODUCTIVITY; QUANTUM YIELD; STRUCTURE ANALYSIS; SYNTHESIS; X RAY DIFFRACTION;

EID: 0043127202     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0346633     Document Type: Article

References (31)

1. For general reviews, see: (a) Ho, T.-L. Tactics of Organic Synthesis; Wiley-Interscience: New York, 1994; p 79.
2. (b) Tietze, L. F. Chem. Rev. 1996, 96, 115.
3. (c) Winkler, J. D. Chem. Rev. 1996, 96, 167.
4. (d) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137.
5. For selected reviews, see: (a) Overman, L. E.; Abelman, M. M.; Kucera, D. J.; Tran, V. D.; Ricca, D. J. Pure Appl. Chem. 1992, 64, 1813.
6. (b) Grigg, R. J Heterocycl. Chem. 1994, 31, 631.
7. (c) de Meijere A.; Meyer, P. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
8. For selected examples, see: (a) Trost, B. M.; Shi, Y. J. Am, Chem., Soc. 1991, 113, 701.
9. (b) Overman, L. E. Ricca, D. J.; Tran, V. D. J. Am. Chem, Soc. 1993, 115, 2042.
10. (c) Trost, B. M.; Shen H. Angew. Chem., Int. Ed. 2001, 40, 2313.
11. (d) Trost, B. M.; Calkins, T. L.; Bochet, C. G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2632.
12. (e) Vorogushin, A. V.; Wulff, W. D.; Hansen, H.-J. J. Am. Chem. Soc. 2002. 124, 6512.
13. For review papers, see: (a) Shore, N. E. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkenson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 703.
14. (b) Geis, O.; Schalz, H. Angew. Chem., Int. Ed. 1998, 37, 911.
15. (a) Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994. 116, 8793.
16. (b) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688.
17. (c) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187.
18. (d) Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249.
19. (e) Morimoto, T.; Chatani, N.; Kukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762.
20. (f) Shiu, Y.-T.; Madhushaw, R. J.; Li, W.-T.; Lee, G.-H.; Peng, S. H.; Liao, F.-L.; Wang, S.-L.; Liu, R.-S., J. Am. Chem. Soc. 1999, 121, 4066.
21. (a) Brummond, K. M.; Lu, J. J. Am. Chem. Soc. 1999, 121, 5087.
22. (b) Tobisu, M.; Chatani, N.; Asaumi, T.; Amako, K.; Ie, Y.; Fukumoto, Y. ; Murai, S. J. Am. Chem. Soc. 2000, 122, 12633.
23. (c) Kablaouni, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 5818.
24. (d) Chatani, N.; Morimoto, T,; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1996, 120, 5335.
25. (e) Chatani, Tobisu, M.; Asaum, T.; Murai, S. Synthesis, 2000, 925.
26. (f) Shibata, T.; Toshida, N.; Takagi, K. Org. Lett. 2002, 4, 1619.
27. -1. See Najdi, S. D.; Olmsteaad, M. M.; Schore, N. E. J. Organomet. Chem. 1992, 431, 335.
28. The ORTEP drawing and crystal data of tricyclic compounds 5, 6, 22b, and 29b are provided in Supporting Information.
29. The ease in the ring-opening of cis-epoxyalkyne is unclear at the present stage. We believe that the vinyl or heteroatom at the cis substituent may coordinate to the cobalt metal to increase its basicity that facilitates the ring-opening of epoxide.
30. For metal-stabilized cyclic allene species, see: (a) Yin, J.; Abboud, K. A.; Jones, W. M. J. Am. Chem. Soc. 1993, 115, 3810.
31. (b) Jones, W. M.; Klosin, J. Adv. Organomet. Chem. 1998, 42, 147.