An improved protocol for the Prins desymmetrisation of cyclohexa-1,4-dienes

Tetrahedron Letters

Volumn 49, Issue 28, 2008, Pages 4446-4448

  Butters, Michael ^b   Elliott, Mark C ^a   Hill Cousins, Joseph ^a   Paine, James S ^a   Westwood, Alexander W J ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; CYCLOHEXA 1,4 DIENE DERIVATIVE; DITERPENE; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CHEMICAL STRUCTURE; ISOMER; METHODOLOGY; PINACOL REARRANGEMENT; STEREOCHEMISTRY;

EID: 44649193089     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.05.022     Document Type: Article

References (52)

1. Snider B.B. In: Trost B.M., Fleming I., and Heathcock C.H. (Eds). Comprehensive Organic Synthesis Vol. 2 (1991), Pergamon Press, New York 527-561
2. Jiménez-Núñez E., Claverie C.K., Nieto-Oberhuber C., and Echavarren A.M. Angew. Chem., Int. Ed. 45 (2006) 5452-5455
3. Barry C.S., Bushby N., Harding J.R., Hughes J.R., Parker G.D., Roe R., and Willis C.L. Chem. Commun. (2005) 3727-3729
4. Jasti R., Vitale J., and Rychnovsky S.D. J. Am. Chem. Soc. 126 (2004) 9904-9905
5. Barry C.St.J., Crosby S.R., Harding J.R., Hughes R.A., King C.D., Parker G.D., and Willis C.L. Org. Lett. 5 (2003) 2429-2432
6. Patterson B., Marumoto S., and Rychnovsky S.D. Org. Lett. 5 (2003) 3163-3166
7. Jaber J.J., Mitsui K., and Rychnovsky S.D. J. Org. Chem. 66 (2001) 4679-4686
8. Tian X., Jaber J.J., and Rychnovsky S.D. J. Org. Chem. 71 (2006) 3176-3183
9. Barry C.S., Elsworth J.D., Seden P.T., Bushby N., Harding J.R., Alder R.W., and Willis C.L. Org. Lett. 8 (2006) 3319-3322
10. Bahnk K.D., and Rychnovsky S.D. Chem. Commun. (2006) 2388-2390
11. Lee C.-H.A., and Loh T.-P. Tetrahedron Lett. 47 (2006) 1641-1644
12. Barry C.S., Bushby N., Charmant J.P.H., Elsworth J.D., Harding J.R., and Willis C.L. Chem. Commun. (2005) 5097-5099
13. Aubele D.L., Wan S., and Floreancig P.E. Angew. Chem., Int. Ed. 44 (2005) 3485-3488
14. Chan K.-P., and Loh T.-P. Org. Lett. 7 (2005) 4491-4494
15. Vitale J.P., Wolckenhauer S.A., Do N.M., and Rychnovsky S.D. Org. Lett. 7 (2005) 3255-3258
16. Barry C.S., Bushby N., Harding J.R., and Willis C.L. Org. Lett. 7 (2005) 2683-2686
17. Kopecky D.J., and Rychnovsky S.D. J. Am. Chem. Soc. 123 (2001) 8420-8421
18. Rychnovsky S.D., and Thomas C.R. Org. Lett. 2 (2000) 1217-1219
19. Overman L.E., and Velthuisen E.J. J. Org. Chem. 71 (2006) 1581-1587
20. Overman L.E., and Velthuisen E.J. Org. Lett. 6 (2004) 3853-3856
21. Overman L.E., and Pennington L.D. J. Org. Chem. 68 (2003) 7143-7157
22. Hanaki N., Link J.T., MacMillan D.W.C., Overman L.E., Trankle W.G., and Wurster J.A. Org. Lett. 2 (2000) 223-226
23. Overman L.E. Acc. Chem. Res. 25 (1992) 352-359
24. Hopkins M.H., Overman L.E., and Rishton G.M. J. Am. Chem. Soc. 113 (1991) 5354-5365
25. For the use of a Prins reaction to desymmetrise a 1,8-diene see:. Rychnovsky S.D., Yang G., Hu Y., and Khire U.R. J. Org. Chem. 62 (1997) 3022-3023
26. Studer A., and Schleth F. Synlett (2005) 3033-3041
27. Villar F., Kolly-Kovac T., Equey O., and Renaud P. Chem. Eur. J. 9 (2003) 1566-1577
28. Villar F., Equey O., and Renaud P. Org. Lett. 2 (2000) 1061-1064
29. Curran D.P., Qi H.Y., and De Mello N.C. J. Am. Chem. Soc. 116 (1994) 8430-8431
30. Curran D.P., Geib S.J., and Lin C.-H. Tetrahedron: Asymmetry 5 (1994) 199-202
31. Lebeuf R., Robert F., Schenk K., and Landais Y. Org. Lett. 8 (2006) 4755-4758
32. Studer A., and Schleth F. Angew. Chem., Int. Ed. 43 (2004) 313-315
33. Schleth F., Vogler T., Harms K., and Studer A. Chem. Eur. J. 10 (2004) 4171-4185
34. Wipf P., Rector S.R., and Takahashi H. J. Am. Chem. Soc. 124 (2002) 14848-14849
35. Nguyen T.M., Seifert R.J., Mowrey D.R., and Lee D. Org. Lett. 4 (2002) 3959-3962
36. Bland D., Hart D.J., and Lacoutiere S. Tetrahedron 53 (1997) 8871-8880
37. Wipf P., Kim Y., and Goldstein D.M. J. Am. Chem. Soc. 117 (1995) 11106-11112
38. Fujioka H., Kitagaki S., Ono N., Kitagawa H., Kita Y., and Matsumoto K. Tetrahedron: Asymmetry 5 (1994) 333-336
39. Wipf P., and Kim Y. Tetrahedron Lett. 33 (1992) 5477-5480
40. Martin S.F., and Campbell C.L. J. Org. Chem. 53 (1988) 3184-3190
41. Martin S.F., Davidsen S.K., and Puckette T.A. J. Org. Chem. 52 (1987) 1962-1972
42. Grainger R.S., Tisselli T., and Steed J.W. Org. Biomol. Chem. 2 (2004) 151-153
43. Carreño M.C., González M.P., and Houk K.N. J. Org. Chem. 62 (1997) 9128-9137
44. Elliott M.C., and El Sayed N.N.E. Tetrahedron Lett. 46 (2005) 2957-2959
45. Elliott M.C., El Sayed N.N.E., and Ooi L.-l. Tetrahedron Lett. 48 (2007) 4561-4564
46. Elliott M.C., El Sayed N.N.E., and Paine J.S. Eur. J. Org. Chem. (2007) 792-803
47. Butters M., Elliott M.C., Hill-Cousins J., Paine J.S., and Walker J.K.E. Org. Lett. 9 (2007) 3635-3638
48. Overman L.E., and Pennington L.D. Org. Lett. 2 (2000) 2683-2686
49. MacMillan D.W.C., and Overman L.E. J. Am. Chem. Soc. 117 (1995) 10391-10392
50. MacMillan D.W.C., Overman L.E., and Pennington L.D. J. Am. Chem. Soc. 123 (2001) 9033-9044
51. Molander G.A., and Jeffrey S.C. Tetrahedron Lett. 43 (2002) 359-362
52. Kim H., Lee H., Kim J., Kim S., and Kim D. J. Am. Chem. Soc. 128 (2006) 15851-15855