Sc(OTf) 3/TsOH: A highly efficient catalytic system for the synthesis of 2,6-dioxabicyclo[3,2,1]octane derivatives

Tetrahedron Letters

Volumn 53, Issue 24, 2012, Pages 3100-3103

  Subba Reddy, B V ^a   Narasimhulu, G ^a   Vikram Reddy, Y ^a   Chakravarthy, P P ^a   Yadav, J S ^a   Sridhar, B ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

2,6 Dioxabicyclo 3,2,1 octane scaffolds; Cascade reactions; Co operative catalysis; Intramolecular Prins cyclization

Indexed keywords

2,6 DIOXABICYCLO[3,2,1]OCTANE DERIVATIVE; ALDEHYDE; BICYCLO[3.2.1]OCTANE DERIVATIVE; DICHLOROETHANE; SCANDIUM; SCANDIUM TRIFLATE; TOLUENESULFONIC ACID DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ACETALIZATION; ARTICLE; CATALYST; CHEMICAL REACTION; CYCLIZATION; SYNTHESIS;

EID: 84861194878     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.04.029     Document Type: Article

References (52)

1. P.E. Linnett, and R.B. Beechey Methods Enzymol. 55 1979 472
2. M.C. Bowden, and G. Pattenden Tetrahedron Lett. 26 1985 4797
3. H.A. Lardy, J.L. Connelly, and D. Johnson Biochemistry 3 1964 1961
4. T. Saishu, Y. Kagawa, and R. Shimizu Biochem. Biophys. Res. Commun. 112 1983 822
5. M.J. van Raaij, J.P. Abrahams, A.G.W. Leslie, and J.E. Walker Proc. Natl. Acad. Sci. U.S.A. 93 1996 6913
6. L.J. Mulheirn, R.B. Beechey, D.P. Leworthy, and M.D. Osselton Chem. Commun. 21 1974 874
7. S. Lai, K. Matsunaga, Y. Shizuri, and S. Yamamura Tetrahedron Lett. 31 1990 5503
8. I.M. Pastor, and M. Yus Curr. Org. Chem. 11 2007 925
9. E.A. Crane, and K.A. Scheidt Angew. Chem., Int. Ed. 49 2010 8316
10. M.R. Gesinski, K. Tadpetch, and S.D. Rychnovsky Org. Lett. 11 2009 5342
11. M.S. Kwon, S.K. Woo, S.W. Na, and E. Lee Angew. Chem., Int. Ed. 47 2008 1733
12. S. Manaviazar, and K.J. Hale Angew. Chem., Int. Ed. 50 2011 8786
13. P.A. Wender, and A.J. Schrier J. Am. Chem. Soc. 133 2011 9228
14. S.K. Woo, M.S. Kwon, and E. Lee Angew. Chem., Int. Ed. 47 2008 3242
15. M.R. Gesinski, and S.D. Rychnovsky J. Am. Chem. Soc. 133 2011 9727
16. H.-Y. Lin, and B.B. Snider Org. Lett. 13 2011 1234
17. C. Olier, M. Kaafarani, S. Gastaldi, and M.P. Bertrand Tetrahedron 66 2010 413
18. C. St. Barry, S.R. Crosby, J.R. Harding, R.A. Hughes, C.D. King, G.D. Parker, and C.L. Willis Org. Lett. 5 2003 2429
19. X.F. Yang, J.T. Mague, and C. Li J. Org. Chem. 66 2001 739
20. U. Reddy, and A.K. Saikia Synlett 2010 1027
21. H. Li, and T.-P. Loh Org. Lett. 12 2010 2679
22. M. Pham, A. Allatabakhsh, and T.G. Minehan J. Org. Chem. 73 2008 741
23. F.K. Chio, J. Warne, D. Gough, M. Penny, S. Green, S.J. Coles, M.B. Hursthouse, P. Jones, L. Hassall, T.M. McGuire, and A.P. Dobbs Tetrahedron 67 2011 5107
24. A.P. Dobbs, S.J.J. Guesne, S. Martinovic, S.J. Coles, and M.B. Hursthouse J. Org. Chem. 68 2003 7880
25. A.P. Dobbs, and S. Martinovic Tetrahedron Lett. 43 2002 7055
26. B. Yu, T. Jiang, J. Li, Y. Su, X. Pan, and X. She Org. Lett. 11 2009 3442
27. D. Clarisse, B. Pelotier, O. Piva, and F. Fache Chem. Commun. 48 2012 157
28. L.F. Silva Jr., and S.A. Quintiliano Tetrahedron Lett. 50 2009 2256
29. M.P. Castaldi, D.M. Troast, and J.A. Porco Jr. Org. Lett. 11 2009 3362
30. K. Tadpetch, and S.D. Rychnovsky Org. Lett. 10 2008 4839
31. M.A. Beaulieu, K.C. Guérard, G. Maertens, C. Sabot, and S. Canesi J. Org. Chem. 76 2011 9460
32. S. Desjardins, J.-C. Andrez, and S. Canesi Org. Lett. 13 2011 3406
33. J.-C. Andrez, M.-A. Giroux, J. Lucien, and S. Canesi Org. Lett. 12 2010 4368
34. M.A. Beaulieu, C. Sabot, N. Achache, K.C. Guerard, and S. Canesi Chem. Eur. J. 16 2010 11224
35. E. Fenster, C. Fehl, and J. Aubé Org. Lett. 13 2011 2614
36. Z.-H. Chen, Y.-Q. Tu, S.-Y. Zhang, and F.-M. Zhang Org. Lett. 13 2011 724
37. A.M. Meyer, C.E. Katz, S.-W. Li, D.V. Velde, and J. Aubé Org. Lett. 12 2010 1244
38. M. Nakamura, K. Niiyama, and T. Yamakawa Tetrahedron Lett. 50 2009 6462
39. J. Tamiya, and E.J. Sorensen Tetrahedron 59 2003 6921
40. Y.S. Cho, H.Y. Kim, J.H. Cha, A.N. Pae, H.Y. Koh, J.H. Choi, and M.H. Chang Org. Lett. 4 2002 2025
41. J.D. Elsworth, and C.L. Willis Chem. Commun. 2008 1587
42. H.-J. Jin, J. Lu, N.-J. Zheng, and X. Wu Gaodeng Xuexiao Huaxue Xuebao 31 2010 514
43. J.S. Yadav, B. Prashant, P.P. Chakravarthy, B.V.S. Reddy, A.V.S. Sarma, S.J. Basha, B. Sridhar, and R. Grée J. Org. Chem. 75 2010 2081
44. B.V.S. Reddy, B. Prashant, J.S. Yadav, B. Sridhar, and R. Grée J. Org. Chem. 76 2011 7677
45. J.S. Yadav, B.V.S. Reddy, T. Maity, and G.G.K.S.N. Kumar Tetrahedron Lett. 48 2007 7155
46. J.S. Yadav, B.V.S. Reddy, G.G.K.S.N. Kumar, and T. Swamy Tetrahedron Lett. 48 2007 2205
47. J.S. Yadav, B.V.S. Reddy, G.G.K.S.N. Kumar, and G.M. Reddy Tetrahedron Lett. 48 2007 4903
48. J.S. Yadav, B.V.S. Reddy, A.V. Ganesh, and G.G.K.S.N. Kumar Tetrahedron Lett. 51 2010 2963
49. J.S. Yadav, P.P. Chakravarthy, B. Prashant, B.V.S. Reddy, and A.V.S. Sarma Tetrahedron Lett. 50 2009 5998
50. ††CCDC-865556 (3j) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
51. N. Greeves, H.C. Aspinall, J.S. Bissett, and D. Levin Tetrahedron Lett. 43 2002 319
52. N. Greeves, H.C. Aspinall, J.S. Bissett, and D. Levin Tetrahedron Lett. 43 2002 323