Acid-catalyzed skeletal rearrangement of epoxy alkynes: A fast access to highly functionalized allenes

Organic Letters

Volumn 11, Issue 15, 2009, Pages 3214-3217

  Zheng, Zhao Jing ^a   Shu, Xing Zhong ^a   Ji, Ke Gong ^a   Zhao, Shu Chun ^a   Liang, Yong Min ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 68149112488     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9014199     Document Type: Article

References (38)

1. (a) Asahara, H.; Kubo, E.; Togaya, K.; Koizumi, T.; Mochizuki, E.; Oshima, T. Org. Lett. 2007, 9, 3421.
2. (b) Hanson, R. M. Chem. Rev. 1991, 91, 437
3. (c) Blay, G.; Cardona, L.; Collado, A. M.; Garca, B.; Pedro, J. R. J. Org. Chem. 2006, 71, 4929.
4. (d) Yamamoto, K.; Heathcock, C. H. Org. Lett. 2000, 2, 1709.
5. (e) Nakatani, M.; Nakamura, M.; Suzuki, A.; Inoue, M.; Katoh, T. Org. Lett. 2002, 4, 4483.
6. (a) Crandall, J. K.; Apparu, M. Org. React. (N.Y.) 1983, 29, 345.
7. (b) Doris, E.; Dechoux, L.; Mioskowski, C. Synlett 1998, 337.
8. (c) Hodgson, D. M.; Gras, E. Synthesis 2002, 1625.
9. (d) Hodgson, D. M.; Gras, E. In Topics in Organometallic Chemistry; Springer: Berlin, Germany, 2003; p 217.
10. (e) Hodgson, D. M.; Bray, C. D. In Aziridine and Epoxides in Organic Synthesis; Wiley-VCH Verlag GmbH & Co. KgaA: Weinheim, Germany, 2006; Chapter 5, p 145.
11. (a) Shen, Y.-M.; Wang, B.; Shi, Y. Angew. Chem., Int. Ed. 2006, 45, 1429.
12. (b) Rami, B. C.; Jana, U. J. Org. Chem. 1998, 63, 8212.
13. (c) Chang, C-L.; Kumar, M. P.; Liu, R.-S. J. Org. Chem. 2004, 69, 2793.
14. (a) Wipf, P.; Maciejewski, J. P. Org. Lett. 2008, 70, 4383.
15. (b) Bournaud, C.; Bonin, M.; Micouin, L. Org. Lett. 2006, 8, 3041.
16. (c) Asahara, H.; Kubo, E.; Togaya, K.; Koizumi, T.; Mochizuki, E.; Oshima, T. Org. Lett. 2007, 9, 3421.
17. (a) Burova, S. A.; McDonald, F. E. J. Am. Chem. Soc. 2004, 126, 2495.
18. (b) Kim, K.; Okamoto, S.; Sato, F. Org. Lett. 2001, 3, 67.
19. (a) Lin, M.-Y.; Maddirala, S. J.; Liu, R.-S. Org. Lett. 2005, 7, 1745.
20. (b) Lin, G.-Y.; Li, C.-W.; Hung, S.-H.; Liu, R.-S. Org. Lett. 2008, 10, 5059.
21. (c) Dai, L.-Z.; Qi, M.-J.; Shi, Y.-L.; Liu, X.-G.; Shi, M. Org. Lett. 2007, 9, 3191.
22. Arcadi, A. Chem. Rev. 2008, 108, 3266.
23. (a) Shu, X.-Z.; Liu, X.-Y.; Ji, K.-G.; Xiao, H.-Q.; Liang, Y.-M. Chem-Eur. J. 2008, 14, 5282.
24. (b) Ji, K.-G.; Shen, Y.-W.; Shu, X.-Z.; Xiao, H.-Q.; Bian, Y.-J.; Liang, Y.-M. Adv. Synth. Catal. 2008, 350, 1275.
25. (c) Ji, K.-G.; Shu, X.-Z.; Chen, J.; Zhao, S.-C; Zheng, Z.-J.; Liu, X.-Y.; Liang, Y.-M. Org. Biomol. Chem. 2009, 7, 2501.
26. (a) Trost, B. M.; Pinkerton, A. B.; Seidel, M. J. Am. Chem. Soc. 2001, 123, 12466.
27. (b) Baner, K. Liebigs Ann. 1997, 2005.
28. (a) Alienes in Organic Synthesis; Schuster, H. F., Coppola, G. M., Eds.; John Wiley & Sons: New York, 1984.
29. (b) The Chemistry of Retenes, Allenes, and Related Compounds, Part 1; Patai, S., Ed.; John Wiley & Sons: New York, 1980.
30. (c) Modern Allene Chemistry; Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, Germany, 2004.
31. Madhushaw, R. J.; Li, C-L.; Shen, K.-H.; Hu, C.-C.; Liu, R.-S. J. Am. Chem. Soc. 2001, 123, 7427.
32. The molecular structure of the corresponding product 2a was determined by X-ray crystallography (Figure 1). Crystallographic data have been described in the Supporting Information.
33. For detailed optimization of reaction conditions, see the Supporting Information.
34. 1H NMR spectroscopic analysis. For a full explanation and definition of the terms syn and anti as used herein see: Marson, C. M.; Benzies, D. W. M.; Hobson, A. D. Tetrahedron 1991, 47, 5491.
35. 1H NMR spectroscopy.
36. (a) Ma, S.-M. Chem. Rev. 2005, 105, 2829.
37. (b) Smith, N. D.; Mancuso, J.; Lautens, M. Chem. Rev. 2000, 100, 3257.
38. (c) Widenhoefer, R. S. Chem,-Eur. J. 2008, 14, 5382.