Highly stereoselective synthesis of 2,5-disubstituted 3-vinylidene tetetrahydrofurans via prins-type cyclization

Organic Letters

Volumn 7, Issue 15, 2005, Pages 3283-3285

  Shin, Chul ^a   Chavre, Satish N ^a   Ae, Nim Pae ^a   Joo, Hwan Cha ^a   Hun, Yeong Koh ^a   Moon, Ho Chang ^a   Jung, Hoon Choi ^b   Yong, Seo Cho ^a  

^a Korea Institute of Science and Technology   (South Korea)

^b Hanyang University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 23044510870     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051058r     Document Type: Article

References (41)

1. (a) For a review, see: Boivin, T. L. B. Tetrahedron 1987, 43, 3309-3362.
2. (b) Wolfe, J. P.; Rossi, M. A. J. Am. Chem. Soc. 2004, 126, 1620-1621.
3. (c).Ajamian, A.; Gleason, J. L. Org. Lett. 2001, 3, 4161-4164.
4. (d) Tiecco, M.; Testaferri, L.; Bagnoli, L.; Purgatorio, V.; Temperini, A.; Marini, F.; Santi, C. Tetraheron: Asymmetry 2004, 15, 405-412.
5. (e) Duan, S.; Moeller, Org. Lett. 2001, 3, 2685-2688.
6. (f) Chirskaya, M. V.; Vasil'ev, A. A.; Sergovskaya, N. L.; Shorshnev, S. V.; Sviridov, S. L. Tetraherdon Lett. 2004, 45, 8811-8813.
7. (g) Ting, P. C.; Bartlett, P. A. J. Am. Chem. Soc. 1984, 106, 2668-2671.
8. (h) Labelle, M.; Guindon, Y. J. Am. Chem. Soc. 1989, 111, 2204-2210.
9. (a) Moinuddin, S. G. A.; Hishiyama, S.; Cho, M.-H.; Davin, L. B.; Lewis, N. G. Org. Biomol. Chem. 2003, 1, 2307-2313.
10. (b) Keum, G.; Kang, S. B.; Kim, Y.; Lee, E. Org. Lett. 2004, 6, 1895-1897.
11. (c) Caller, M. A.; Zhu, C. J. Org. Chem. 1999, 64, 1415-1419.
12. (d) Walkup, R. D.; Mosher, M. D. Tetrahedron 1993, 49, 9285-9294.;
13. (e) Lee, E.; Jeong, E. J, Kang, E. J.; Sung, L. T.; Hong, S. K. J. Am. Chem. Soc. 2001, 123, 10131-10132.
14. (f) Cohen, F.; MacMillan, D. W. C.; Overman, L. E.; Romero, A. Org. Lett. 2001, 3, 1225-1228.
15. (g) Meyer, C.; Cossy, J. Tetrahedron Lett. 1997, 38, 7861-7864.
16. (h) Ericsson, C.; Engman, L. Org. Lett. 2001, 3, 3459-3462.
17. (i) McCarthy, D. G.; Collins, C. C.; O'Driscoll, J. P.; Lawrence, S. E. J. Chem. Soc., Perkin Trans. 1 1999, 3667-3675.
18. (j) Shi, H. S.; Liu, H.; Bloch, R.; Mandville, G. Tetrahedron 2001, 57, 9335-9341.
19. (k) Overman, L. E.; Pennington, L. D. J. Org. Chem. 2003, 68, 7143-7157.
20. (a) Cho, Y. S.; Karupaiyan, K.; Kang, H. J.; Cha, J. H.; Pae, A. N.; Koh, H. Y.; Chang, M. H. Chem. Commun. 2003, 2346-2347.
21. (b) Cho, Y. S.; Kim, H. Y.; Cha, J. H.; Pae, A. N.; Koh, H. Y.; Choi, J. H.; Chang, M. H. Org. Lett. 2002, 4, 2025-2028.
22. (c) Kang, H. J.; Kim, S. H.; Pae, A. N.; Koh, H. Y.; Chang, M. H.; Choi, K. I.; Han, S.-Y.; Cho, Y. S. Synlett 2004, 14, 2545-2548.
23. (d) Jasti, R.; Vitale, J.; Rychnovsky, S. D. J. Am. Chem. Soc. 2004, 126, 9904-9905.
24. (e) Rychnovsky, S. D.; Thomas, C. R. Org. Lett. 2000, 2, 1217-1219.
25. (d) Yadav, V. K.; Kumar, N. V. J. Am. Chem. Soc. 2004, 126, 8652-8653.
26. (d) Yang, J.; Viswanathan, G. S.; Li, C-J. Tetrahedron Lett. 1999, 40, 1627-1630.
27. (e) Viswanathan, G. S.; Yang, J.; Li, C-J. Org. Lett. 1999, 1, 993-995.
28. (f) Li, C-J.; Zhang, W-C. Tetrahedron 2000, 56, 2403-2411.
29. (g) Yang, X- F.; Mague, J. T.; Li, C-J. J. Org. Chem. 2001, 66, 739-747.
30. (h) Li, J.; Li, C-J. Tetrahedron Lett. 2001, 42, 793-796.
31. (i) Frater, G.; Muller, U.; Kraft, P. Helv. Chim. Acta 2004, 87, 2750-2763.
32. (j) Mohr, P. Tetrahedron Lett. 1993, 34, 6251-6254.
33. (k) Marko, I. E.; Bayston, D. J. Tetraheron Lett. 1993, 34, 6595-6598.
34. (l) Marko, I. E.; Mekhalfia, A.; Bayston, D. J.; Adams, H. J. J. Org. Chem. 1992, 57, 2211-2213.
35. (a) Han, Y.; Huang, Y. Z. Tetrahedron Lett. 1994, 35, 9433-9434.
36. (b) Loh, T. P.; Lin, M. J.; Tan, K. L. Tetrahedron Lett. 2003, 44, 507-509.
37. (c) Henk, H.; Speckamp, W. N. Tetrahedron Lett. 1983, 24, 1407-1410.
38. For a review, see: Rhebtaranonth, C.; Thebtaranonth, Y. Tetrahedron 1990, 46, 1385-1489.
39. The cis relationship identification was determined by NOE experiments.
40. Canonne, P.; Foscolos, G. B.; Belanger, D. J. Org. Chem. 1980, 45, 1828-1835.
41. Bauer, V. J.; Ong, H. H.; Kosley, R. W., Jr. J. Heterocycl. Chem. 1982, 19, 1069-1072.