Novel synthesis of 3-(3,3,3-trifluoroprop-1-en-2-yl)furans via stereoselective processing and palladium-catalyzed cycloisomerization

Tetrahedron Letters

Volumn 48, Issue 11, 2007, Pages 1911-1913

  Zhang, Jiming ^a   Zhao, Xiaoming ^a   Lu, Long ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Cyclization isomerization; Furan; Palladium; Trifluoromethyl

Indexed keywords

FURAN DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ISOMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

TRIFLUORO;

EID: 33846894737     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.01.097     Document Type: Article

References (27)

1. Lipshutz B.H. Chem. Rev. 86 (1986) 795-819
2. Brown R.C.D. Angew. Chem. 117 (2005) 872-874
3. Angew. Chem., Int. Ed. 44 (2005) 850-852
4. Welch J.T. Tetrahedron 43 (1987) 3123-3197
5. Liu Y.S., Purrington S.T., and Huang W.Y. J. Org. Chem. 63 (1998) 5623-5626
6. McAtee J.J., Schinazi R.F., and Liotta D.C. J. Org. Chem. 63 (1998) 2161-2167
7. Jiang J., DeVita R.J., Doss G.A., Goulet M.T., and Wyvratt M.J. J. Am. Chem. Soc. 121 (1999) 593-594
8. Smith J.O., Mandal B.K., Filler R., and Beery J.W. J. Fluorine Chem. 81 (1997) 123-128
9. Burger K., and Helmreich B. J. Chem. Soc., Chem. Commun. (1992) 348-349
10. Bambury R.E., Yaktin H.K., and Wyckoff K.K. J. Heterocycl. Chem. 5 (1968) 95
11. Forrest A.K., and O'hanlon P.J. Tetrahedron Lett. 36 (1995) 2117-2118
12. Sham H.L., and Betebenner D.A. J. Chem. Soc., Chem. Commun. (1991) 1134-1135
13. Fukuda Y., Shiragami H., Utimoto K., and Nozaki H. J. Org. Chem. 56 (1991) 5816-5819
14. Gabriele B., Salerno G., and Lauria E. J. Org. Chem. 64 (1999) 7687-7692
15. Ma S.M., Lu L.H., and Zhang J.L. J. Am. Chem. Soc. 126 (2004) 9645-9660
16. Marshall J.A., and Sehon C.A. J. Org. Chem. 60 (1995) 5966-5968
17. Seiller B., Bruneau C., and Dixneuf P.H. J. Chem. Soc., Chem. Commun. (1994) 493-494
18. Seiller B., Bruneau C., and Dixneuf P.H. Tetrahedron 51 (1995) 13089-13102
19. Marshall J.A., and DuBay W.J. J. Org. Chem. 58 (1993) 3435-3443
20. Marshall J.A., and DuBay W.J. J. Org. Chem. 59 (1994) 1703-1708
21. Marshall J.A., and Bennett C.E. J. Org. Chem. 59 (1994) 6110-6113
22. Li Y.H., Lu L., and Zhao X.M. Org. Lett. 6 (2004) 4467-4470
23. Li Y.H., Zhao X.M., and Lu L. J. Fluorine Chem. 125 (2004) 1821-1824
24. Zhang J., Zhao X., Li Y., and Lu L. Tetrahedron Lett. 47 (2006) 4737-4739
25. 3 as the external standard, and downfield shifts being designed as negative.
26. 3O: 314.0919. Found: 314.0930.
27. Crystallographic data for X-ray structure have been deposited with the Cambridge Crystallographic Centre as CCDC 258472. Copies of the data can be obtained free of charge via from the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge CB 1EZ, UK; e-mail: deposit@ccdc.cam.ac.uk.