Direct synthesis of tetrahydropyrans via one-pot Babier-Prins cyclization of allylbromide with carbonyl compounds promoted by RTILs BPyX/SnX′2 or BBIMBr/SnBr2

Tetrahedron

Volumn 62, Issue 29, 2006, Pages 7113-7120

  Zhao, Xian Liang ^a   Liu, Li ^a   Chen, Yong Jun ^a   Wang, Dong ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

Allylbromide; Babier Prins cyclization; BBIMBr SnBr2; Carbonyl compound; Direct synthesis; Tetrahydropyran

Indexed keywords

BROMINE DERIVATIVE; CARBONYL DERIVATIVE; SOLVENT; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; ONE POT SYNTHESIS; PRIORITY JOURNAL; SUBSTITUTION REACTION;

EID: 33744946571     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.04.075     Document Type: Article

References (45)

1. Ohuchida S., Hamanaka N., and Hayashi M. Tetrahedron 39 (1983) 4257-4261
2. Kale V.N.D., and Clive L.J. J. Org. Chem. 49 (1984) 1554-1563
3. Bhagwat S.S., Hamann P.R., Still W.C., Buntiny S., and Fitzpatric F.A. Nature 315 (1985) 511-513
4. For reviews of the Prins reaction, see:
5. Arundale E., and Mikeska L.A. Chem. Rev. 51 (1952) 505-555
6. Adams D.R., and Bhatnagar S.R. Synthesis (1977) 661-672
7. Snider B.B. In: Trost B.M. (Ed). Comprehensive Organic Synthesis Vol. 2 (1991), Pergamon, Oxford 527-561
8. Miles R.B., Davis C.E., and Coates R.M. J. Org. Chem. 71 (2006) 1493-1501
9. Hart D.J., and Bennett C.E. Org. Lett. 5 (2003) 1499-1502 and references cited therein
10. Patterson B., Marumoto S., and Rychnovsky S.D. Org. Lett. 5 (2003) 3163-3166
11. Yadav J.S., Rajasekhar K., and Murty M.S.R. Tetrahedron Lett. 46 (2005) 2311-2314
12. Miranoda L.S.M., and Vasconcellos M.L.A. Synthesis (2004) 1767-1770
13. Yang J., Viswanathan G.S., and Li C.-J. Tetrahedron Lett. 40 (1999) 1627-1630
14. Li J., and Li C.-J. Heterocycles 53 (2000) 1691-1695
15. Zhang W.-C., Viswanathan G.S., and Li C.-J. Chem. Commun. (1999) 291-292
16. Zhang W.-C., and Li C.-J. Tetrahedron 56 (2000) 2403-2411
17. Keh C.C.K., Namboodiri V.V., Varma R.S., and Li C.-J. Tetrahedron Lett. 43 (2002) 4993-4996
18. Sabitha G., Reddy K.B., Kiran Kumar Reddy G.S., Fatima N., and Yadav J.S. Synlett (2005) 2347-2351
19. For review, see:. Yamamoto Y., and Asao N. Chem. Rev. 93 (1993) 2207-2293
20. Wei Z.Y., Li J.S., Wang D., and Chan T.H. Tetrahedron Lett. 28 (1987) 3441-3444
21. Wei Z.Y., Wang D., Li J.S., and Chan T.H. J. Org. Chem. 54 (1989) 5768-5774
22. Coppi L., Ricci A., and Taddi M. J. Org. Chem. 53 (1988) 911-913
23. Chan K.-P., and Loh T.-K. Tetrahedron Lett. 45 (2004) 8387-8390
24. Gambaro A., Boaretto A., Marton D., and Tagliavini G. J. Organomet. Chem. 254 (1983) 293-304
25. Gambaro A., Boaretto A., Marton D., and Tagliavini G. J. Organomet. Chem. 260 (1984) 255-262
26. Boaretto A., Furlani D., Marton D., Tagliavini G., and Gambaro A. J. Organomet. Chem. 299 (1986) 157-167
27. Marton D., Tagliavini G., Zordan M., and Wardell J.L. J. Organomet. Chem. 390 (1990) 127-138
28. Marton D., Tagliavini G., and Zordan M. J. Organomet. Chem. 391 (1990) 295-305
29. Tanaka T. Solvent-free Organic Synthesis (2003), Wiley-VCH, Weinheim
30. For review, see:. Cave G.W.V., Raston C.L., and Scott J.L. Chem. Commun. (2001) 2159-2169
31. For examples, see:
32. Imai T., and Nishida S. J. Chem. Soc., Chem. Commun. (1994) 277-278
33. Tan X.-H., Shen B., Deng W., Zhao H., Liu L., and Guo Q.-X. Org. Lett. 5 (2003) 1833-1835
34. Jang T.S., Keum G., Kang S.B., Chung B.Y., and Kim Y. Synthesis (2003) 775-779
35. Masuyama Y., Kaneko Y., and Kurusu Y. Tetrahedron Lett. 45 (2004) 8969-8971
36. Masuyama Y., Kishida M., and Kurusu Y. Tetrahedron Lett. 37 (1996) 7103-7106
37. Masuyama Y., Ito A., and Kurusu Y. Chem. Commun. (1998) 315-316
38. Masuyama Y., Ito T., Tachi K., Ito A., and Kurusu Y. Chem. Commun. (1999) 1261-1262
39. Ito A., Kishida M., Kurusu Y., and Masuyama Y. J. Org. Chem. 65 (2000) 494-498
40. Wasserscheid P., and Waffenschmidt H. J. Mol. Catal. A: Chem. 164 (2000) 61-67
41. Abbott A.P., Capper G., Davies D.L., Munro H.L., Rasheed R.K., and Tambyrajah V. Chem. Commun. (2001) 2010-2011
42. Abbott A.P., Capper G., Davies D.L., Rasheed R.K., and Tambyrajah V. Green Chem. 4 (2002) 24-26
43. Parshall G.W. J. Am. Chem. Soc. 94 (1972) 8716-8719
44. Tang L., Ding L., Chang W.-X., and Li J. Tetrahedron Lett. 47 (2006) 303-306
45. Ghosh A.K., Shin D., and Schiltz G. Heterocycles 58 (2002) 659-666 and references cited therein