A mild and efficient selective tetrahydropyranylation of primary alcohols and deprotection of THP ethers of phenols and alcohols using PdCl 2(CH3CN)2 as catalyst

Tetrahedron Letters

Volumn 45, Issue 14, 2004, Pages 2973-2976

  Wang, Yan Guang ^a   Wu, Xiao Xing ^a   Jiang, Zhi Yong ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALLYL COMPOUND; BENZENE DERIVATIVE; BENZYL DERIVATIVE; CARBONYL DERIVATIVE; ETHER DERIVATIVE; PALLADIUM COMPLEX; PHENOL DERIVATIVE; TETRAHYDROFURAN;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; DEPROTECTION REACTION; ROOM TEMPERATURE; TETRAHYDROPYRANYLATION;

EID: 1642328121     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.02.057     Document Type: Article

References (63)

1. Greene T.W., Wuts P.G.M. Protective Groups in Organic Synthesis. 3rd ed. 1999;John Wiley and Sons, New York. pp 49-54.
2. Kocienski P.J. Enders D., Noyori R., Trost B.M. Protecting Groups. 1994;83-85 Georg Thieme, Stuttgart.
3. Creenhalgh C.W., Henbest H.B., Jones E.R.H. J. Chem. Soc. 1951;1190-1193.
4. Ott A.C., Murray M.F., Pederson R.L. J. Am. Chem. Soc. 74:1952;1239-1241.
5. Jones R.G., Mann M.J. J. Am. Chem. Soc. 75:1953;4048-4052.
6. Miyashita M., Yoshikoshi A., Grieco P.A. J. Org. Chem. 42:1977;3772-3774.
7. Torii S., Inokuchi T., Kondo K., Ito H. Bull. Chem. Soc. Jpn. 58:1985;1347-1348.
8. Bolitt V., Mioskowski C., Shin D.S., Falck J.R. Tetrahdron Lett. 29:1988;4583-4586.
9. Yadav J.S., Srinivas D., Reddy G.S. Synth. Commun. 28:1998;1399-1404.
10. Branco L.C., Afonso C.A.M. Tetrahedron. 57:2001;4405-4410.
11. Hon Y.-S., Lee C.-F., Chen R.-J., Szu P.-H. Tetrahedron Lett. 57:2001;5991-6001.
12. Naik S., Gopinath R., Patel B.K. Tetrahedron Lett. 42:2001;7679-7681.
13. Ravindranath N., Ramesh C., Das B. Synlett. 2001;1777-1778.
14. Romanelli G.P., Baronetti G., Thomas H.J., Autino J.C. Tetrahedron Lett. 43:2002;7589-7591.
15. Alper H., Dinkes L. Synthesis. 1972;81.
16. Namboodiri V.V., Varma R.S. Tetrahedron Lett. 43:2002;1143-1146.
17. Karimi B., Maleki J. Tetrahedron Lett. 43:2002;5353-5355.
18. Brown D.S., Ley S.V., Vile S., Thompson M. Tetrahedron. 47:1991;1329-1342.
19. Tanemura K., Horaguchi T., Suzuki T. Bull. Chem. Soc. Jpn. 65:1992;304-305.
20. Deka N., Sarma J.C. J. Org. Chem. 66:2001;1947-1948.
21. Iqbal J., Srivastava R.R., Gupta K.B., Khan M.A. Synth. Commun. 19:1989;901-906.
22. Bhuma V., Kantam M.L. Synth. Commun. 22:1992;2941-2944.
23. Maity G., Roy S.C. Synth. Commun. 23:1993;1667-1671.
24. Kantam M.L., Santhi P.L. Synth. Commun. 23:1993;2225-2228.
25. Ma S., Venanzi L.M. Tetrahedron Lett. 34:1993;5269-5272.
26. Bhalerao U.T., Davis K.J., Rao B.V. Synth. Commun. 26:1996;3081-3085.
27. Molnar A., Beregszaszi T. Tetrahedron Lett. 37:1996;8597-8600.
28. Habibi M.H., Tangesaninejad S., Mohammadpoor-Baltork I., Mirkhani V., Yadollahi B. Tetrahedron Lett. 57:2001;2851-2853.
29. Pachamuthu K., Vankar Y.D. J. Org. Chem. 66:2001;7511-7513.
30. Mineno T. Tetrahedron Lett. 43:2002;7975-7978.
31. Bongini A., Cardillo G., Orena M., Sandri S. Synthesis. 1979;618-620.
32. Menger F.M., Chu C.H. J. Org. Chem. 46:1981;5044-5045.
33. Olah G.A., Husain A., Singh B.P. Synthesis. 1983;892-895.
34. Hoyer S., Laszlo P., Orlovic M., Polla E. Synthesis. 1986;655-657.
35. Johnston R.D., Marston C.R., Krieger P.E., Goe G.L. Synthesis. 1988;393-394.
36. Patney H.K. Synth. Commun. 21:1991;2329-2333.
37. Chavez F., Godinez R. Synth. Commun. 22:1992;159-164.
38. Campelo J.M., Garcia A., Lafont F., Luna D., Marinas J.M. Synth. Commun. 22:1992;2335-2342.
39. Kumar P., Dinesh C.U., Reddy R.S., Pandey B. Synthesis. 1993;1069-1070.
40. Campelo J.M. Synth. Commun. 24:1994;1345-1350.
41. Bandgar B.P., Jagtap S.R., Aghade B.B., Wadgaonkar P.P. Synth. Commun. 25:1995;2211-2215.
42. Upadhya T.T., Daniel T., Sudalai A., Ravindranathan T., Sabu K.R. Synth. Commun. 26:1996;4539-4544.
43. Bauduin G., Bondon D., Pietrasanta Y., Pucci B. Tetrahedron. 34:1978;3269-3274.
44. Corey E.J., Niwa H., Knolle J. J. Am. Chem. Soc. 100:1978;1942-1943.
45. Ogawa Y., Shibasaki M. Tetrahedron Lett. 25:1984;663-664.
46. Otera J., Nozaki H. Tetrahedron Lett. 27:1986;5743-5746.
47. Kim S., Park J.H. Tetrahedron Lett. 28:1987;439-440.
48. Wagner A., Heitz M.P., Mioskowski C. J. Chem. Soc., Chem. Commun. 1989;1619-1620.
49. Nambiar K.P., Mitra A. Tetrahedron Lett. 35:1994;3033-3036.
50. Zimmermann K. Synth. Commun. 25:1995;2959-2962.
51. Maiti G., Roy S.C. J. Org. Chem. 61:1996;6038-6039.
52. Mechelke M.F., Wiemer D.F. J. Org. Chem. 64:1999;4821-4829.
53. Taniguchi T., Kadoka K., ElAzab A.S., Ogasawara K. Synlett. 1999;1247-1248.
54. Heravi M.M., Ajami D., Mojtahedi M.M., Ghassemzadeh M. Tetrahedron Lett. 40:1999;561-562.
55. Marko I.E., Ates A., Augustyns B., Gautier A., Quesnel Y., Turet Y., Wiaux M. Tetrahedron Lett. 40:1999;5613-5616.
56. Tanemur K., Suzuki T., Horaguchi T. Bull. Chem. Soc. Jpn. 67:1994;290-292.
57. Raina S., Singh V.K. Synth. Commun. 25:1995;2395-2400.
58. Srikrishna A., Sattigeri J.A., Viswajanani R., Yelamaggad C.V. J. Org. Chem. 60:1995;2260.
59. Lipshutz B.H., Pollart D., Monforte J., Kotsuki H. Tetrahedron Lett. 26:1985;705-708.
60. Wilson N.S., Keay B.A. Tetrahedron Lett. 37:1996;153-156.
61. 4) and solvent removal, the crude product was purified by flash column chromatography over silica gel using ethyl acetate/hexane (1:20) as eluent to afford the corresponding THP ether 2 (188 mg, 91%).
62. 4) and solvent removal, the crude product was purified by flash column chromatography over silica gel using ethyl acetate/hexane (1:20) as eluent to afford the corresponding alcohol 1 (113 mg, 93%).
63. Wabnitz T.C., Yu J.Q., Spencer J.B. Chem. Eur. J. 10:2004;484-493.