Diastereoselective synthesis of substituted tetrahydrothiopyrans via (3,5)-thionium-ene cyclization reaction

Journal of Organic Chemistry

Volumn 77, Issue 5, 2012, Pages 2508-2512

  Bondalapati, Somasekhar ^a   Gogoi, Paramartha ^a   Indukuri, Kiran ^a   Saikia, Anil K ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BORON TRIFLUORIDE ETHERATE; CYCLIZATION REACTIONS; DIASTEREO-SELECTIVITY; DIASTEREOSELECTIVE SYNTHESIS; GOOD YIELD;

ALDEHYDES; BORON; CYCLIZATION;

STEREOSELECTIVITY;

5 METHYLHEX 4 ENE 1 THIOL; ALDEHYDE; BORON TRIFLUORIDE; TETRAHYDROPYRAN DERIVATIVE; THIOL DERIVATIVE; THIOL GROUP; THIONIUM; UNCLASSIFIED DRUG;

(3,5) THIONIUM ENE CYCLIZATION; ARTICLE; CONTROLLED STUDY; CYCLIZATION; DIASTEREOISOMER; ISOMERIZATION; MOLECULAR STABILITY; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

ALDEHYDES; CYCLIZATION; MOLECULAR STRUCTURE; PYRANS; QUATERNARY AMMONIUM COMPOUNDS; STEREOISOMERISM; SULFHYDRYL COMPOUNDS;

EID: 84857891389     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2023944     Document Type: Article

References (49)

1. Woodward, R. B.; Heusler, K.; Gosteli, J.; Naegeli, P.; Oppolzer, W.; Ramage, R.; Ranganathan, S.; Vorbrüggen, H. J. Am. Chem. Soc. 1966, 88, 852-853
2. Casy, G.; Lane, S.; Taylor, R. J. K. J. Chem. Soc., Perkin. Trans. 1 1986, 1397-1404
3. Ohuchida, S.; Hamanaka, N.; Hayashi, M. Tetrahedron 1983, 39, 4273-4278
4. Gal'pern, G. D. Int. J. Sulfur Chem., B. 1971, 6, 115-130
5. Payzant, J. D.; Cyr, T. D.; Montgomery, D. S.; Strausz, O. P. Tetrahedron Lett. 1985, 26, 4175-4178
6. Mehta, S.; Andrews, J. S.; Johnston, B. D.; Svensson, B.; Pinto, B. M. J. Am. Chem. Soc. 1995, 117, 9783-9790
7. Block, E. Reactions of Organosulfur Compounds: Academic Press: New York, 1978.
8. Woodward, R. B.; Logusch, E.; Nambiar, K. P.; Sakan, K.; Ward, D. E.; Au-Yeung, B. W.; Balaram, P.; Browne, L. J.; Card, P. J.; Chen, C. H. J. Am. Chem. Soc. 1981, 103, 3210-3213
9. Almena, J.; Foubelo, F.; Yus, M. Tetrahedron 1997, 53, 5563-5572
10. Agarwal, V. K.; Smith, H. W.; Hynd, G.; Jones, R. V. H.; Fieldhouse, R.; Spey, S. E. J. Chem. Soc., Perkin Trans. 1 2000, 3267-3276
11. Boger, D. L.; Weinerb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987.
12. Gademann, K.; Chavez, D. E.; Jacobson, E. N. Angew. Chem., Int. Ed. 2002, 41, 3059-3061
13. Gouverneur, V.; Reiter, M. Chem.-Eur. J. 2005, 11, 58065815
14. Gademann, K.; Chavez, D. E.; Jacobson, E. N. Angew. Chem., Int. Ed. 2005, 44, 3485-3488
15. Desimoni, G.; Faita, G.; Toscanini, M.; Boiocchi, M. Chem.-Eur. J. 2007, 13, 9478-9485
16. Paterson, I.; Steven, A.; Luckhurst, C. A. Org. Biomol. Chem. 2004, 2, 3026-3038
17. Liu, P.; Jacobson, E. N. J. Am. Chem. Soc. 2001, 123, 10772-10773
18. Voight, E. A.; Seradj, H.; Roethle, P. A.; Burke, S. D. Org. Lett. 2004, 6, 4045-4048
19. Ruijter, E. R.; Schltingkemper, H.; Wessjohann, L. A. J. Org. Chem. 2005, 70, 2820-2823
20. Clarke, P. A.; Santos, S.; Martin, W. H. C. Green. Chem. 2007, 9, 438-440
21. Clarke, P. A.; Martin, W. H. C.; Hargreaves, M. J.; Wilson, C.; Blake, A. J. Org. Biomol. Chem. 2005, 3, 3551-3563
22. Avery, T. D.; Caiazza, D.; Culbert, J. A.; Taylor, D. K.; Tiekink, R. T. J. Org. Chem. 2005, 70, 8344-8351
23. Yadav, J. S.; Reddy, B. V. S.; Maity, T.; Kumar, G. G. K. S. Tetrahedron Lett. 2007, 48, 7155-7159
24. Chan, K.-P.; Seow, A.-H.; Loh, T.-P. Tetrahedron Lett. 2007, 48, 37-41
25. Yadav, J. S.; Reddy, B. V. S.; Kumar, G. G. K. S. N.; Swamy, T. Tetrahedron Lett. 2007, 48, 2205-2208
26. Yang, X.-F.; Mague, J. T.; Li, C.-J. J. Org. Chem. 2001, 66, 739-747
27. Yang, X.-F.; Li, C.-J. Tetrahedron Lett. 2000, 41, 1321-1325
28. Ozaki, S.; Matsui, E.; Yoshinaga, H.; Kitagawa, S. Tetrahedron Lett. 2000, 41, 2621-2624
29. Rosiak, A.; Frey, W.; Christoffers, J. Eur. J. Org. Chem. 2006, 4044-4054
30. Weïwer, M.; Coulombel, L.; Duñach, E. Chem. Commun. 2006, 332-334
31. Weïwer, M.; Chaminade, X.; Bayón, J. C.; Duñach, E. Eur. J. Org. Chem. 2007, 2464-2469
32. Tamura, Y.; Choi, H.-D.; Shindo, H.; Uenishi, J.; Ishibashi, H. Tetrahedron Lett. 1981, 22, 81-84
33. Blumenkopf, T. A.; Look, G. C.; Overman, L. E. J. Am. Chem. Soc. 1990, 112, 4399-4403
34. Overman, L. E. Acc. Chem. Res. 1992, 25, 352-359
35. Overman, L. E.; Thompson, A. S. J. Am. Chem. Soc. 1988, 110, 2248-2256
36. Sonawane, H. R.; Maji, D. K.; Jana, G. H.; Pandey, G. Chem. Commun. 1998, 1773-1774
37. Sasmal, P. K.; Maier, M. E. J. Org. Chem. 2003, 68, 824-831
38. Ohmura, H.; Smyth, G. D.; Mikami, K. J. Org. Chem. 1999, 64, 6056-6059
39. Mikami, K.; Ohmura, H.; Yamanaka, M. J. Org. Chem. 2003, 68, 1081-1088
40. Ohmura, H.; Mikami, K. Tetrahedron Lett. 2001, 42, 6859-6863
41. Loh, T.-P.; Hu, Q.-Y.; Tan, K.-T.; Cheng, H.-S. Org. Lett. 2001, 3, 2669-2672
42. Saha, P.; Reddy, U. C.; Bondalapati, S.; Saikia, A. K. Org. Lett. 2010, 12, 1824-1826
43. Saha, P.; Gogoi, P.; Saikia, A. K. Org. Biomol. Chem. 2011, 9, 4626-4634
44. Bondalapati, S.; Reddy, U. C.; Saha, P.; Saikia, A. K. Org. Biomol. Chem. 2011, 9, 3428-3438
45. Reddy, U. C.; Raju, B. R.; Kumar, E. K. P.; Saikia, A. K. J. Org. Chem. 2008, 73, 1628-1630
46. Reddy, U. C.; Bondalapati, S.; Saikia, A. K. Eur. J. Org. Chem. 2009, 1625-1629
47. Reddy, U. C.; Bondalapati, S.; Saikia, A. K. J. Org. Chem. 2009, 74, 2605-2608
48. Reddy, U. C.; Saikia, A. K. Synlett 2010, 1027-1032
49. Stach, D.; Zheng, Y. F.; Perez, A. L.; Oehlschlager, A. C. J. Med. Chem. 1997, 40, 201-209