A fast and practical approach to tetrahydropyranylation and depyranylation of alcohols using indium triflate

Tetrahedron Letters

Volumn 43, Issue 44, 2002, Pages 7975-7978

  Mineno, Tomoko ^a,b  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

Acetylation; Alcohols; Depyranylation; Indium triflate; Tetrahydropyranylation

Indexed keywords

ACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; ETHER DERIVATIVE; INDIUM; METHANOL; REAGENT; TETRAHYDROPYRAN DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL MODIFICATION; REACTION ANALYSIS;

EID: 0037190862     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01864-6     Document Type: Article

References (35)

1. Greene T.W., Wuts P.G.M. Protective Groups in Organic Synthesis. 3rd ed. 1999;John Wiley & Sons, New York.
2. Kocienski P.J. Protecting Groups. 2000;Georg Thieme Verlag, New York.
3. Deka N., Sarma J.C. J. Org. Chem. 66:2001;1947-1948.
4. Branco L.C., Afonso C.A.M. Tetrahedron. 57:2001;4405-4410.
5. Babu B.S., Balasubramanian K.K. Synlett. 1999;1261-1262.
6. Nishiguchi T., Hayakawa S., Hirasaka Y., Saitoh M. Tetrahedron Lett. 41:2000;9843-9846.
7. Curini M., Epifano F., Marcotullio M.C., Rosati O., Costantino U. Tetrahedron Lett. 39:1998;8159-8162.
8. Babu B.S., Balasubramanian K.K. Tetrahedron Lett. 39:1998;9287-9288.
9. Davis K.J., Bhalerao U.T., Rao B.V. Synth. Commun. 30:2000;2301-2308.
10. Marko I.E., Ates A., Augustyns B., Gautier A., Quesnel Y., Turet L., Wiaux M. Tetrahedron Lett. 40:1999;5613-5616.
11. Ramasamy K.S., Bandaru R., Averett D. Synth. Commun. 29:1999;2881-2894.
12. Bernady K.F., Floyd M.B., Poletto J.F., Weiss M.J. J. Org. Chem. 44:1979;1438-1446.
13. Corey E.J., Niwa H., Knolle J. J. Am. Chem. Soc. 100:1978;1942-1943.
14. Miyashita M., Yoshikoshi A., Grieco P.A. J. Org. Chem. 42:1977;3772-3774.
15. Yadav J.S., Srinivas D., Reddy G.S. Synth. Commun. 28:1998;1399-1404.
16. Rezai N., Meybodi F.A., Salehi P. Synth. Commun. 30:2000;1799-1805.
17. Deka N., Sarma J.C. Synth. Commun. 30:2000;4435-4441.
18. Kumar H.M.S., Reddy B.V.S., Reddy E.J., Yadav J.S. Chem. Lett. 1999;857-858.
19. Habibi M.H., Tangestaninejad S., Mohammadpoor-Baltork I., Mirkhani V., Yadollahi B. Tetrahedron Lett. 42:2001;2851-2853.
20. Reddy M.A., Reddy L.R., Bhanumathi N., Rao K.R. Synth. Commun. 30:2000;4323-4328.
21. Hon Y.-S., Lee C.-F. Tetrahedron Lett. 40:1999;2389-2392.
22. Naik S., Gopinath R., Patel B.K. Tetrahedron Lett. 42:2001;7679-7681.
23. Valluri M., Mineno T., Hindupur R.M., Avery M.A. Tetrahedron Lett. 42:2001;7153-7154.
24. Mineno T., Choi S.-R., Avery M.A. Synlett. 2002;883-886.
25. Yadav J.S., Subba Reddy B.V., Srinivasa Rao R., Veerendhar G., Nagaiah K. Tetrahedron Lett. 42:2001;8067-8070.
26. Loh T.-P., Hu Q.-Y., Tan K.-T., Cheng H.-S. Org. Lett. 3:2001;2669-2672.
27. Prajapati D., Laskar D.D., Sandhu J.S. Tetrahedron Lett. 41:2000;8639-8643.
28. Gadhwal S., Sandhu J.S. J. Chem. Soc., Perkin 1. 2000;2827-2829.
29. Chauhan K.K., Frost C.G., Love I., Waite D. Synlett. 1999;1743-1744.
30. Trost B.M., Portnoy M., Kurihara H. J. Am. Chem. Soc. 119:1997;836-837.
31. 4. The mixture was filtered and then concentrated by rotary evaporation. Purification by flash chromatography using hexanes/ethyl acetate (9:1) furnished the THP ether of benzyl alcohol (151 mg, 85% yield).
32. 4. The mixture was filtered and concentrated by rotary evaporation. Purification by flash chromatography using hexanes/ethyl acetate (8:2) yielded the corresponding alcohol (52 mg, 93% yield).
33. 4. The mixture was filtered and concentrated by rotary evaporation. Purification by flash chromatography using hexanes/ethyl acetate (8:2) furnished benzyl acetate (73 mg, 94% yield).
34. Ranu B.C., Hajra A. J. Chem. Soc., Perkin Trans. 1. 2001;2262-2265.
35. Chandra K.L., Saravanan P., Singh V.K. Tetrahedron Lett. 42:2001;5309-5311.