Sc(OTf)3-catalyzed one-pot ene-Prins cyclization: a novel synthesis of octahydro-2H-chromen-4-ols

Tetrahedron Letters

Volumn 51, Issue 22, 2010, Pages 2963-2966

  Yadav, J S ^a   Reddy, B V Subba ^a   Ganesh, A V ^a   Narayana Kumar, G G K S ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Aldehydes; Citronellal; ene Prins cyclization; Isopulegol; Octahydro 2H chromen 4 ols

Indexed keywords

1 NAPHTHALDEHYDE; 2 NITROBENZALDEHYDE; 4 ANISALDEHYDE; 4 BROMOBENZALDEHYDE; 4 CHLOROBENZALDEHYDE; 4 TOLURALDEHYDE; CHEMICAL COMPOUND; CINNAMALDEHYDE; CITRONELLAL; CYCLOHEXANECARBALDEHYDE; HYDROCINNAMALDEHYDE; ISOVELARALDEHYDE; OCTAHYDRO 2H CHROMEN 4 OL DERIVATIVE; PROPANALDEHYDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ENVIRONMENTAL TEMPERATURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 77951253840     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.03.100     Document Type: Article

References (65)

1. Walsh D.P., and Chang Y.-T. Chem. Rev. 106 (2006) 2476
2. Arya P., Chou D.T.H., and Baek M.-G. Angew. Chem., Int. Ed. 40 (2001) 339
3. Kotame P., Horng B.-C., and Liao J.-H. Tetrahedron Lett. 50 (2009) 704
4. Schreiber S.L. Science 287 (2000) 1964
5. Posner G.H. Chem. Rev. 86 (1986) 831
6. Ho T.-L. Tandem Organic Reactions (1992), Wiley-Interscience, New York
7. Hall N. Science 266 (1994) 32
8. Tietze L.F. Chem. Rev. 96 (1996) 115
9. Montgomery J. Angew. Chem., Int. Ed. 43 (2004) 3890
10. Negishi E., Coperet C., Ma S., Liou S.Y., and Liu F. Chem. Rev. 96 (1996) 365
11. Grigg R., and Sridharan V. J. Organomet. Chem. 65 (1999) 576
12. Miura T., and Murakami M. Chem. Commun. (2007) 217
13. Agapiou K., Cauble D.F., and Krische M.J. J. Am. Chem. Soc. 126 (2004) 4528
14. Subburaj K., and Montgomery J. J. Am. Chem. Soc. 125 (2003) 11210
15. Guo H.C., and Ma J.A. Angew. Chem., Int. Ed. 45 (2006) 354
16. Enders D., Huttl M.R.M., Grondal C., and Raabe G. Nature 441 (2006) 861
17. Cabrera S., Alemen J., Bolze P., Bertelsen S., and Jørgensen K.A. Angew. Chem., Int. Ed. 47 (2008) 121
18. Penon O., Carlone A., Mazzanti A., Locatelli M., Sambri L., Bartoli G., and Melchiorre P. Chem. Eur. J. 14 (2008) 4788
19. Barluenga J., Fernandez A., Dieguez A., Rodriguez F., and Fananas F.J. Chem. Eur. J. 15 (2009) 11660
20. Chavre S.N., Ullapu P.N., Min S.-J., Lee J.K., Pae A.N., Kim Y., and Cho Y.S. Org. Lett. 11 (2009) 3834
21. Ullapu P.N., Min S.-J., Chavre S.N., Choo H., Lee J.K., Pae A.N., Kim Y., Chang M.H., and Cho Y.S. Angew. Chem., Int. Ed. 48 (2009) 2196
22. Elliott M.C., Sayed N.N.E.E., and Paine J.S. Eur. J. Org. Chem. (2007) 792
23. Epstein O.L., and Rovis T. J. Am. Chem. Soc. 128 (2006) 16480
24. Pham M., Allatabakhsh A., and Minehan T.G. J. Org. Chem. 73 (2008) 741
25. Li H., and Loh T.P. J. Am. Chem. Soc. 130 (2008) 7194
26. Gesinski, M. R.; Tadpetch, K.; Rychnovsky, S. D. Org. Lett. 2009, ASAP.
27. Zhao X.-L., Liu L., Chen Y.-J., and Wang D. Tetrahedron 62 (2006) 7113
28. Yadav J.S., Subba Reddy B.V., Narayana Kumar G.G.K.S., and Madhusudhan Reddy M. Tetrahedron Lett. 48 (2007) 4903
29. Yadav J.S., Reddy B.V.S., Kumar G.M., and Murthy Ch.V.S.R. Tetrahedron Lett. 42 (2001) 89
30. Crosby S.R., Harding J.R., King C.D., Parker G.D., and Willis C.L. Org. Lett. 4 (2002) 3407
31. Dobbs A.P., and Martinovic S. Tetrahedron Lett. 43 (2002) 7055
32. Aubele D.L., Lee C.A., and Floreancig P.E. Org. Lett. 5 (2003) 4521
33. Liu F., and Loh T.-P. Org. Lett. 9 (2007) 2063
34. Tadpetch K., and Rychnovsky S.D. Org. Lett. 10 (2008) 4839
35. Miranda P.O., Carballo R.M., Marti{dotless}n V.S., and Padron J.I. Org. Lett. 11 (2009) 357
36. Yadav J.S., Subba Reddy B.V., Narayana Kumar G.G.K.S., and Swamy T. Tetrahedron Lett. 48 (2007) 2205
37. Yadav J.S., Subba Reddy B.V., Narayana Kumar G.G.K.S., and Reddy M.G. Tetrahedron Lett. 48 (2007) 4903
38. Yadav J.S., Subba Reddy B.V., Maity T., and Narayana Kumar G.G.K.S. Tetrahedron Lett. 48 (2007) 7155
39. Yadav J.S., Subba Reddy B.V., Maity T., and Narayana Kumar G.G.K.S. Tetrahedron Lett. 48 (2007) 8874
40. Yadav J.S., Subba Reddy B.V., Aravind S., Narayana Kumar G.G.K.S., Madhavi C., and Kunwar A.C. Tetrahedron 64 (2008) 3025
41. Yadav J.S., Subba Reddy B.V., Narayana Kumar G.G.K.S., and Aravind S. Synthesis 48 (2008) 395
42. Bahnck K.B., and Rychnovsky S.D. J. Am. Chem. Soc. 130 (2008) 13177
43. Woo S., Kwon M.S., and Lee E. Angew. Chem., Int. Ed. 47 (2008) 3242
44. Cossey K.N., and Funk R.L. J. Am. Chem. Soc. 126 (2004) 12216
45. Chan K.-P., Ling Y.H., and Loh T.-P. Chem. Commun. (2007) 939
46. Wender P.A., DeChristopher B.A., and Schrier A.J. J. Am. Chem. Soc. 130 (2008) 6658
47. Aubele D.L., Wan S., and Floreancig P.E. Angew. Chem., Int. Ed. 44 (2005) 3485
48. Lee C.-H.A., and Loh T.-P. Tetrahedron Lett. 47 (2006) 1641
49. Yadav J.S., Padmavani B., Reddy B.V.S., Venugopal Ch., and Rao A.B. Synlett (2007) 2045
50. Yadav J.S., Thrimurtulu N., Gayathri K.U., Reddy B.V.S., and Prasad A.R. Tetrahedron Lett. 49 (2008) 6617
51. Yadav J.S., Lakshmi K.A., Reddy N.M., Prasad A.R., and Reddy B.V.S. Tetrahedron 44 (2010) 334
52. Yadav J.S., and Narayana Kumar G.G.K.S. Tetrahedron 66 (2010) 480
53. Snider B.B. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 2 (1991), Pergamon, Oxford, UK 527
54. Mikami K., and Shimizu M. Chem. Rev. 92 (1992) 1021
55. Mikami K., Terada M., Narisawa S., and Nakai T. Synlett (1992) 255
56. Snider B.M. Acc. Chem. Res. 13 (1980) 426
57. Trost B.M. Acc. Chem. Res. 23 (1990) 34
58. Marshall J.A., and Andersen M.W. J. Org. Chem. 57 (1992) 5851
59. Marshall J.A., and Andersen M.W. J. Org. Chem. 58 (1993) 3912
60. Braddock D.C., Hii K.K., and Brown J.M. Angew. Chem. 37 (1998) 1720
61. Eliel E.L., Willen S.H., and Mander L.N. Stereochemistry of Organic Compounds (1994), J. Wiley & Sons, New York
62. Lenardao E.J., Botteselle G.V., Azambuja F.D., Perin G., and Jacob R.G. Tetrahedron 63 (2007) 6671
63. Aggarwal V.K., Vennall G.P., Davey P.N., and Newman C. Tetrahedron Lett. 39 (1998) 1997
64. Silva Jr. L.F., and Quintiliano S.A. Tetrahedron Lett. 50 (2009) 2256
65. 4. Removal of the solvent followed by purification on silica gel (Merck, 60-120 mesh, ethyl acetate-hexane, 1.0-9.0) gave the pure products.