Ruthenium-catalyzed cyclic carbonylation of allenyl alcohols. Selective synthesis of γ- and δ-lactones

Organic Letters

Volumn 2, Issue 4, 2000, Pages 441-443

  Yoneda, Eiji ^a   Kaneko, Takayuki ^a   Zhang, Shi Wei ^a   Onitsuka, Kiyotaka ^a   Takahashi, Shigetoshi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001613006     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990377d     Document Type: Article

References (35)

1. For a review, see: (a) Schore N. E. Chem. Rev. 1988, 88, 1081.
2. (b) Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation: Direct Synthesis of carbonyl Compounds; Plenum Press: New York, 1991.
3. (c) Stille, J. K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, p 913.
4. (d) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
5. (e) Ungvary, F. Coord. Chem. Rev. 1998, 170, 245.
6. (a) Urata, H.; Yugari, H.; Fuchikami, T. Chem. Lett. 1987, 833.
7. (b) Ohe, K.; Takahashi, H.; Uemura, S.; Sugita, N. J. Org. Chem. 1987, 52, 4859.
8. (c) Matsuda, I.; Ogiso, A.; Sato, S. J. Am. Chem. Soc. 1990, 112, 6120.
9. (d) Ali, E. B.; Alper, H. J. Org. Chem. 1991, 56, 5357.
10. (e) Matsushita, K.; Komori, T.; Oi, S.; Inoue, Y. Tetrahedron Lett. 1994, 35, 5889.
11. (f) Ali, E. B.; Okuro, K.; Vasapollo, G. Alper, H. J. Am. Chem. Soc. 1996, 118, 4264.
12. (g) Xiao, W.; Alper, H. J. Org. Chem. 1997, 62, 3422.
13. (h) Yu, W.; Alper, H. J. Org. Chem. 1997, 62, 5684.
14. (i) Gabriele, B.; Salerno, G.; De Pascali, F.; Costa, M. Chiusoli, G. P. J. Chem. Soc., Perkin Trans. 1 1997, 147.
15. (j) Ogawa, A.; Kawabe, K.; Kawakami, J.; Mihara, M.; Hirao, T.; Sonoda, N. Organometallics 1998, 17, 3111.
16. (k) Yoneda, E.; Sugioka, T.; Hirao, K.; Zhang, S.; Takahashi, S. J. Chem. Soc., Perkin Trans. 1 1998, 477.
17. (l) Yoneda, E.; Kaneko, T.; Zhang, S.; Takahashi, S. Tetrahedron Lett. 1998, 39, 5061.
18. (m) Zhang, X.; Cao, P. J. Am. Chem. Soc. 1999, 121, 7708.
19. (a) Matsuda, I.; Sakakibara, J.; Nagashima, H. Tetrahedron Lett. 1991, 32, 7431.
20. (b) Hirao, K.; Morii, K.; Joh, T. Takahashi, S. Tetrahedron Lett. 1995, 36, 6243.
21. (c) Delgado, R. A.; Rosa, R. G.; Mavarez, E. J. Mol. Catal. 1996, 108, 125.
22. (d) Bacchi, A.; Chiusoli, G. P.; Costa, M.; Gabriele, B.; Righi, C.; Salerno, G. J. Chem. Soc., Chem. Commun. 1997, 1209.
23. (a) Ojima, I.; Tzamarioudaki, M.; Tsai, C. J. Am. Chem. Soc. 1994, 116, 3643.
24. (b) Sugioka, T.; Zhang, S.; Morii, N.; Joh, T.; Takahashi, S. Chem. Lett. 1996, 249.
25. (a) Kudo, K.; Oida, Y.; Mitsuhashi, K.; Mori, S.; Komatsu, K.; Sugita, N. Bull. Chem. Soc. Jpn. 1996, 69, 1337.
26. (b) Sugioka, T. Yoneda, E.; Onitsuka, K.; Zhang, S.; Takahashi, S. Tetrahedron Lett. 1998, 38, 4989.
27. (a) Nakanishi, K.; Goto, T.; Ito, S. Natural Product Chemistry; Kodansya: Tokyo, 1974; Vols. 1-3.
28. (b) Dictionary of Natural Products, 1st ed.; Buckingham, J., Ed.; Chapman & Hall: New York. 1994.
29. (a) The Chemistry of Ketenes, Allenes, and Related Compounds; Patai, S., Ed.; John Wiley & Sons: New York, 1980; Part 1.
30. (b) Schuster, H. F.; Coppola, G. M. Allenes in Organic Synthesis; John Wiley & Sons: New York, 1988.
31. Ma, S.; Shi, Z.; J. Org. Chem. 1998, 63, 6387.
32. (a) Satyanarayana, N.; Alper, H.; Amer, I. Organometallics 1990, 9, 284.
33. (b) Piotti, M. E.; Alper, H. J. Am. Chem. Soc. 1994, 59, 1956.
34. (c) Xiao, W.-J.; Giuseppe, V.; Alper, H. J. Org. Chem. 1998, 63, 2609.
35. All new compounds were identified by NMR, IR, mass spectral analyses, and elemental analyses. See the Supporting Information.