2-Phenylthio-3-bromopropene, a valuable synthon, easily prepared by a simple rearrangement

Organic Letters

Volumn 8, Issue 10, 2006, Pages 2087-2090

  Chen, Wenbo ^a   Zhao, Xiaoming ^a   Lu, Long ^a   Cohen, Theodore ^b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33744745604     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0605171     Document Type: Article

References (36)

1. Masuyama, Y.; Sano, T.; Oshima, M.; Kurusu, Y. Bull. Chem. Soc. Jpn. 2003, 76, 1679-1690.
2. A number of experimental details were not included in ref 1.
3. 1,2-Rearrangements of phenylthio groups to carbocationic centers: Warren, S. Acc. Chem. Res. 2002, 35, 401-406.
4. 1
5. 1
6. Janicki, S. Z.; Fairgrieve, J. M.; Petillo, P. A. J. Org. Chem. 1998, 63, 3694-3700 and references therein.
7. Yasuda, M.; Tsuji, S.; Shigeyoshi, Y.; Baba, A. J. Am. Chem. Soc. 2002, 124, 7440-7447.
8. Srikrishna, A.; Viswajanani, R.; Sattigeri, J. A. Tetrahedron: Asymmetry 2003, 14, 2975-2983.
9. Negishi, E.; Matsushita, H.; Chatterjee, S.; John, R. A. J. Org. Chem. 1982, 47, 3188-3190.
10. Jacobson, R. M.; Raths, R. A.; McDonald, J. H., III. J. Org. Chem. 1977, 42, 2545-2549.
11. The diketone 10 was prepared by allylation of the metalloenamine of cycloheptanone with 2-methoxy-3-bromopropene, mixed with byproducts from the difficult preparation of the latter, and subsequent hydrolysis.
12. Imagawa, H.; Kurisaki, T.; Nishizawa, M. Org. Lett. 2004, 6, 3679-3681.
13. α-Acetonyl ketones and their equivalents are known to form such furans upon acid treatment, (a) Gingerich, S. B.; Jennings, P. W. J. Org. Chem. 1983, 46, 2606-2608.
14. (b) Nienhouse, E. J.; Irwin, R. M.; Finni, G. R. J. Am. Chem. Soc. 1967, 89, 4557-4558.
15. (a) Deng, K.; Bensari, A.; Cohen, T. J. Am. Chem. Soc. 2002, 124, 12106-12107.
16. (b) Deng, K.; Bensari-Bouguerra, A.; Whetstone, J.; Cohen, T. J. Org. Chem. 2006, 71, 2360-2372.
17. Avasthi, K.; Salomon, R. G. J. Org. Chem. 1986, 51, 2556-2562.
18. Bailey, W. F.; Mealy, M. J.; Wiberg, K. B. Org. Lett. 2002, 4, 791-794.
19. (a) Piffl, M.; Weston, J.; Gunther, W.; Anders, E. J. Org. Chem. 2000, 65, 5942-5950 and citations therein.
20. (b) Warren, S. Acc. Chem. Res. 2002, 35, 401-406.
21. (c) Freeman, R.; Haynes, R. K.; Loughlin, W. A.; Mitchell, C.; Stokes, J. V. Pure Appl. Chem. 1993, 65, 647-54.
22. (d) Cohen, T.; Bhupathy, M. Acc. Chem Res. 1989, 22, 152-161.
23. (e) McCullough, D. W.; Bhupathy, M.; Piccolino, E.; Cohen, T. Tetrahedron 1991, 47, 9727-9736.
24. (f) Cabral, J. A.; Cohen, T.; Doubleday, W. W.; Duchelle, E. F.; Fraenkel, G.; Guo, B.-S.; Yü, S. H. J. Org. Chem. 1992, 57, 3680-3684.
25. (g) Cheng, D.; Knox, K. R.; Cohen, T. J. Am. Chem. Soc. 2000, 122, 412-413.
26. (h) Maercker, A.; Jaroschek, H.-J. J. Organomet. Chem. 1976, 116, 21-37.
27. (i) Cheng, D.; Zhu, S.; Yu, Z.; Cohen, T. J. Am. Chem. Soc. 2001, 123, 30-34.
28. (j) Denmark, S. E.; Weber, E. J.; Wilson, T. M.; Willson, T. M. Tetrahedron 1989, 45, 1053-1065 and citations therein (EN 1262).
29. (k) Keck, G. E.; Cressman, E. N. K.; Enholm, E. J. J. Org. Chem. 1989, 54, 4345-4349 and citations therein.
30. (l) Evans, D. A.; Andrews, G. C. Acc. Chem. Res. 1974, 7, 147-155.
31. (m) Kosarych, Z.; Cohen, T. Tetrahedron Lett. 1982, 23, 3019-3022 and citations therein.
32. (n) Cohen, T.; Kosarych, Z. J. Org. Chem. 1982, 47, 4005-4007.
33. (o) Mura, A. J., Jr.; Bennett, D. A.; Cohen, T. Tetrahedron Lett. 1975, 4433-4436.
34. (a) Simpkins, N. S. Sulphones in Organic Synthesis; Pergamon: New York, 1993.
35. (b) Deng, K.; Chalker, J.; Yang, A.; Cohen, T. Org. Lett. 2005, 7, 3637-3640.
36. Padwa, A.; Bullock, W. H.; Dyszlewski, A. D. J. Org. Chem. 1990, 55, 955-964.