Palladium(0) Cyclisation of 1-Aryl-6-hydroxy-2-hexynyl Carbonates: A New Way to Dihydropyrans

Synlett

Volumn 1996, Issue 6, 1996, Pages 553-554

  Fournier Nguefack, Christelle ^a   Lhoste, Paul ^a   Sinou, Denis ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001771530     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5477     Document Type: Article

References (32)

1. Trost, B. M.; Verhoeven, T. R. In Comprehensive Organometallic Chemistry; Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon Press: New York, 1982, 8, 799.
2. (a) Trost, B. M. Acc. Chem. Res. 1980, 13, 385.
3. (b) Trost, B. M. Chemtracts-Organic Chemistry 1988, 1, 415.
4. (c) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173.
5. Godleski, S. A. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991, 4, 585.
6. (a) Tsuji, J. Organic Synthesis with Palladium Compounds, Springer-Verlag: Berlin, 1980.
7. (b) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140.
8. (c) Tsuji, J. Tetrahedron 1986, 42, 4361.
9. (d) Tsuji, J. Palladium Reagents and Catalysts; Innovations in Organic Synthesis, John Wiley & Sons: Chichester, 1995.
10. Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985.
11. Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257.
12. Frost, C. G.; Howarth, J; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089.
13. Harrington, P. J. In Comprehensive Organometallic Chemistry II, Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: Oxford, 1995, 12, 797.
14. (a) Tsuji, J.; Watanabe, H.; Minami, I; Shimizu, I. J. Am. Chem. Soc. 1985, 107, 2196.
15. (b) Tsuji, J.; Sugiura, T.; Minami, I. Tetrahedron Lett. 1986, 27, 731.
16. (c) Minami, I.; Yuhara, M.; Tsuji, J. Tetrahedron Lett. 1987, 28, 629.
17. (d) Minami, I.; Yuhara, M.; Watanabe, H.; Tsuji, J. J. Organomet. Chem. 1987, 334, 225.
18. (e) Mandai, T.; Kunitomi, H.; Higashi, K.; Kawada, M.; Tsuji, J. Synlett, 1991, 697.
19. (f) Mandai, T.; Susuki, S.; Ikawa, A.; Murakami, T.; Kawada, M.; Tsuji, J. Tetrahedron Lett. 1991, 32, 7687.
20. (g) Geng, L.; Lu, X. J. Chem. Soc., Perkin Trans. I 1992, 17.
21. (h) Mandai, T.; Tsuji, J.; Tsujiguchi, Y.; Saito, S. J. Am. Chem. Soc. 1993, 115, 5865.
22. (i) Mandai, T.; Tsujiguchi, Y.; Matsuoka, S.; Saito, S.; Tsuji, J. J. Organomet. Chem. 1995, 488, 127.
23. (a) Goux, C.; Lhoste, P., Sinou, D. Synlett 1992, 725.
24. (b) Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1992, 33, 8099.
25. (c) Lakhmiri, R.; Lhoste, P.; Kryczka, B.; Sinou, D. J. Carbohydr. Chem. 1993, 12, 223.
26. (d) Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron 1994, 50, 10321.
27. (d) Goux, C.; Lhoste, P.; Sinou, D.; Muzart, J. Sulfur Letters, 1994, 18, 1.
28. (e) Goux, C.; Massacret, M.; Lhoste, P.; Sinou, D. Organometallics 1995, 14, 4585.
29. (f) Sinou, D.; Frappa, I.; Lhoste, P.; Porwanski, S.; Kryczka, B. Tetrahedron Lett., 1995, 36, 1251.
30. 3 and 0.15 mol of dppb in 5 mL of tetrahydrofuran. After being stirred at 50 °C for 24 h, the solvent was removed in vacuo and the crude product chromatographed on silica gel using ethyl acetate petroleum ether as the eluent to give the unsaturated dihydropyran 3.
31. 4), 150.3 (=C<).
32. Busacca, C. A.; Swestock, J.; Johnson, R. E.; Bailey, T. R.; Musza, L.; Rodger, C. A. J. Org. Chem. 1994, 59, 7553.