Ionic liquid promoted interrupted Feist-Benary reaction with high diastereoselectivity

Tetrahedron Letters

Volumn 49, Issue 31, 2008, Pages 4613-4617

  Ranu, Brindaban C ^a   Adak, Laksmikanta ^a   Banerjee, Subhash ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

Diastereoselectivity; Dihydrofurans; Furans; Interrupted Feist Benary reaction; Ionic liquid

Indexed keywords

1 BUTYL 3 METHYLIMIDAZOLIUM HYDROXIDE; FURAN DERIVATIVE; HYDROXIDE; HYDROXYDIHYDROFURAN DERIVATIVE; IONIC LIQUID;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ROOM TEMPERATURE; STEREOCHEMISTRY;

EID: 45049088586     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.05.083     Document Type: Article

References (27)

1. Feist F. Chem. Ber. 35 (1902) 1537-1544
2. Benary E. Chem. Ber. 44 (1911) 489-492
3. Lipshutz B.H. Chem. Rev. 86 (1986) 795-819
4. Lee J., Li J.-H., Oya S., and Snyder J.K. J. Org. Chem. 57 (1992) 5301-5312
5. Kubo I., Lee Y.W., Balogh-Nair V., Nakanishi K., and Chapya A. Chem. Commun. (1976) 949-950
6. Schulte G., Scheuer P.J., and McConnell O.J. Helv. Chim. Acta 63 (1980) 2159-2167
7. Dunlop A.P., and Hurd C.D. J. Org. Chem. 15 (1950) 1160-1164
8. Mross G., Holtz E., and Langer P. J. Org. Chem. 71 (2006) 8045-8049 and references cited therein
9. Cantlon I.J., Cocker W., and McMurry T.B.H. Tetrahedron 15 (1961) 46-52
10. Calter M.A., and Zhu C.. Org. Lett. 4 (2002) 205-208
11. Ying J., Ying L.X., Lin J., Wei H., Li S.X., and Yong Z.S. Chirality 19 (2007) 386-390
12. Calter M.A., Phillips R.M., and Flaschenriem C.. J. Am. Chem. Soc. 127 (2005) 14566-14567
13. Welton T. Chem. Rev. 99 (1999) 2071-2084
14. Wasserscheid P., and Keim W. Angew. Chem., Int. Ed. 39 (2000) 3772-3789
15. Wilkes J.S. Green Chem. 4 (2002) 73-80
16. Parvulescu V.I., and Hardacre C. Chem. Rev. (2007) 2615-2665
17. Namboordiri V.V., and Varma R.S. Chem. Commun. (2002) 342-343
18. Sun W., Xia C.-G., and Wang H.-W. Tetrahedron Lett. 44 (2003) 2409-2411
19. Qiao K., and Yokoyama C. Chem. Lett. 33 (2004) 472-473
20. Earle M.J., Katdare S.P., and Seddon K.R. Org. Lett. 6 (2004) 707-710
21. Ranu B.C., Saha A., and Banerjee S. Eur. J. Org. Chem. (2008) 519-523
22. Ranu B.C., Jana R., and Sowmiah S. J. Org. Chem. 72 (2007) 3152-3154 and references cited therein
23. 13C NMR, HRMS) (see Supplementary data).
24. 2 = 0.1206, GOF = 1.069 for all 5189 reflections. X-ray single crystal data were collected using Mo Kα (λ = 0.7107 Å) radiation on a SMART APEX diffractometer equipped with a CCD area detector. The structure was solved by direct methods and refined in a routine manner. C(7) was found to be disordered between two positions and was refined using the second variable (FVAR) facility of shelxtl software.
25. Lee Y.R., and Yoon S.H. Synth. Commun. 36 (2006) 1941-1951
26. Stetter H., and Jones F. Synthesis (1981) 626-628
27. Mann J., Holland H.J., and Lewis T. Tetrahedron 43 (1987) 2533-2542