Diverse cyclization catalyzed by in(OTf)3 for the convergent assembly of substituted tetrahydrofurans and tetrahydropyrans

Organic Letters

Volumn 3, Issue 17, 2001, Pages 2669-2672

  Loh, Teck Peng ^a   Hu, Qi Ying ^a   Tan, Kui Thong ^a   Cheng, Hin Soon ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0001397224     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016228o     Document Type: Article

References (43)

1. For reviews, see: (a) Bartlett, P. A. Tetrahedron 1980, 36, 2.
2. (b) Bartlett, P. A. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Part B, Chapter 6.
3. (c) Boivin, T. L. Tetrahedron 1987, 43, 3309. For some recent examples, see:
4. (d) Trost, B. M.; Sharma, S.; Schmidt, T. J. Am. Chem. Soc. 1992, 114, 7903.
5. (e) Mikami, K.; Shimizu, M. Tetrahedron Lett. 1992, 33, 6315.
6. (f) Hatano, M.; Terada, M.; Mikami, K. Angew. Chem., Int. Ed. 2001, 40, 249.
7. (g) Yang, J.; Li, C.-J. Synlett 1999, 717.
8. (h) Viswanathan, G. S.; Yang, J.; Li, C.-J. Org. Lett. 1999, 1, 993.
9. (i) Lolkema, L. D. M.; Hiemstra, H.; Semeyn, C.; Speckamp, W. N. Tetrahedron 1994, 50, 7115.
10. (j) Hopkins, M. H.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 4748.
11. (k) Hopkins, M. H.; Overman, L. E.; Rishton, G. M. J. Am. Chem. Soc. 1991, 113, 5354.
12. (l) Nakamura, M.; Toganoh, M.; Wang, X. Q.; Yamago, S.; Nakamura, E. Chem. Lett. 2000, 664.
13. For a review, see: Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
14. For a review, see: (a) Overman, L. E. Ace. Chem. Res. 1992, 25, 352. For examples, see:
15. (b) Blumenlopf, T. A.; Look, G. C.; Overman, L. E. J. Am. Chem. Soc. 1990, 112, 4399.
16. Ohmura, H.; Smyth, G. D.; Mikami, K. J. Org. Chem. 1999, 64, 6056.
17. Loh, T.-P.; Hu, Q.-Y.; Ma, L.-T. J. Am. Chem. Soc. 2001, 123, 2450.
18. For recent reviews, see: (a) Chauhan, K. K.; Frost, C. G. J. Chem. Soc., Perkin Trans. 1 2000, 3015.
19. (b) Babu, G.; Perumal, P. T. Aldrichimica Acta 2000, 33, 16.
20. 3 see:
21. (d) Trost, B. M.; Chan, D. M. J. Am. Chem. Soc. 1983, 105, 2326.
22. (e) Loh, T.-P.; Chua, G.-L.; Vittal, J. J.; Wong, M.-W. Chem. Commun. 1998, 861.
23. (f) Prajapati, D.; Laskar, D. D.; Sandhu, J. S. Tetrahedron Lett. 2000, 41, 8639.
24. (g) Ali, T.; Chauhan, K. K.; Frost, C. G. Tetrahedron Lett. 1999, 40, 5621.
25. (h) Chauhan, K. K.; Frost, C. G.; Love, I.; Waite, D. Synlett 1999, 1743.
26. (i) Gadhwal, S.; Sandhu, J. S. J. Chem. Soc., Perkin Trans. 1 2000, 2827.
27. These two pathways are not mechanistically distinct. For reviews, see: (a) Oppolzer, W.; Snieckus, V. Angew. Chem., Int. Ed. Engl 1978, 17, 476.
28. (b) Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: London, 1991; Vol. 2, pp 527-661.
29. 2 = 0.1213, GOF = 1.005 for 7428 observations with I > 2σ(I).
30. For examples of stepwise Lewis acid catalyzed ene reactions, see: (a) Snider, B. B.; Rodini, D. J.; Kirk, T. C.; Cordova, R. J. Am. Chem. Soc. 1982, 104, 555.
31. (b) Snider, B. B.; Ron, E. J. Am. Chem. Soc. 1985, 107, 8160.
32. For a review, see: (a) Wovkulich, P. M. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: London, 1991; Vol. 1, pp 843-899. For some examples of 1,3-shift, see:
33. (b) Bhupathy, M.; Cohen, T. J. Am. Chem. Soc. 1983, 105, 6978.
34. (c) Thies, R. W.; Daruwala, K. P. J. Org. Chem. 1987, 52, 3798.
35. (a) Cloninger, M. J.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 1092.
36. (b) Olah, G. A.; Prakash, G. K. S.; Sommer, J. Superacids; Wiley: New York, 1985.
37. (c) Farcasiu, D.; Marino, G.; Miller, G.; Kastrup, R. V. J. Am. Chem. Soc. 1989, 111, 7210.
38. Only freshly opened TfOH (within 7 days) was found to give the desired product, thus rendering TfOH an inconvenient catalyst to use.
39. Yang, X.-F.; Mague, J.-T.; Li, C.-J. J. Org. Chem. 2001, 66, 739.
40. For reviews, see: (a) Arya, P.; Chou, D. T. H.; Beak, M.-G. Angew. Chem., Int. Ed. 2001, 40, 339,
41. (b) Liu, D. R.; Schultz, P. G. Angew. Chem., Int. Ed. 1999, 38, 36.
42. (c) Schreiber, S. L. Science 2000, 287, 1964.
43. (d) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed 2001, 40, 2004.