Formal [4+3] epoxide cascade reaction via a complementary ambiphilic pairing strategy

Organic Letters

Volumn 12, Issue 6, 2010, Pages 1216-1219

  Rolfe, Alan ^a   Samarakoon, Thiwanka B ^a   Hanson, Paul R ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; SULFONAMIDE; THIAZEPINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CYCLIZATION; EPOXY COMPOUNDS; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFONAMIDES; THIAZEPINES;

EID: 77949824264     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100035e     Document Type: Article

References (45)

1. (a) Nicolaou, K. C.; Chen, L S. Chem. Soc. Rev. 2009, 38. 2993-3009.
2. (b) Enders, D.; Grndal, C.; Hüttl, M. R. M. Aneew. Chem.. Int. Ed. 2007, 46, 1570-1581.
3. (c) Tietze, L. F.; Beifuss, U. Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163.
4. (a) Tietze, L. F.; Brasche, G.; Gericke, K. M., Eds.; Domino Reactions in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2006.
5. (b) Fustero, S.; Jiménez, D.; Sánchez-Reselló, M.; del Pozo, C. J. Am Chem. Soc. 2007, 129, 6700-6701.
6. (c) Bi, H.-P.; Liu, X.-Y.; Gou, F.-R.; Guo, L.-N-; Duan, X.-H.; Shu, X.-Z.; Liang, Y.-M. Aneew. Chem.. Int. FA 2007, 46, 7068-7071.
7. (d) Rolfe, A.; Young, K.; Hanson, P. R. Eur. J. Org. Chem. 2008, 31, 5254-5262.
8. (a) Bontemps, S.; Gornitzka, H.; Bouhadir, G.; Miqueu, K.; Bourissou, D. Angew. Chem., Int. Ed. 2006, 45, 1611-1614.
9. (b) Bontemps, S.; Bouhadir, G.; Miqueu, K.; Bourissou, D. J. Am. Chem. Soc. 2006, 128, 12056-12057.
10. (c) Tejedor, D.; Méndez-Abt, G.; González-Platas, J.; Ramirez, M. A.; Garc'a-Tellado, F. Chem. Commun. 2009, 2368-2370.
11. (d) Kozytska, M. V.; Dudley, G. B. Chem, Commun 2005, 3047-3049.
12. Molecules containing both electrophilic and nucelophilic nodes also have been defined as amphoteric molecules by Yudin, see: (a) Hili, R.; Yudin, A. K. J. Am. Chem. Soc. 2009, 131, 16404-16406.
13. (b) Hili R.; Yudin, A. K. Angew. Chem., Int. Ed. 2008,47, 4188-4191.
14. (c) Baktharaman, S.; Hili, R.; Yudin, A. K. Aldrichim. Acta 2008, 41, 109-119. Molecules containing both electrophilic and nucleophilic nodes also have been defined as amphiphilic molecules, see:
15. (d) Nakamura, H.; Shim, J.-G.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8113-8114.
16. (e) Nakamura, H.; Aoyagi, K.; Shim, J.-G.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 372-377.
17. (f) Kimura, M.; Tamaki, T.; Nakata, M.; Tohyama, K.; Tamaru, Y. Aneew. Chem., Int. Ed. 2008, 120, 5887-5889.
18. Sultams, the cyclic analogues of sulfonamides, although not found in nature, represent a subclass of relatively unexplored molecular space for the discovery of new therapeutic drugs. Recent reports have demonstrated that sultams possess a broad, spectrum of biological activity. For an extensive list of biological sultams and methods for synthesis see: Jimenez-Hopkins, M.; Hanson, P. R. Ore. Lett. 2008, 10, 2223-2226.
19. (a) Corey, E. J.; Russey, W. E.; Ortiz de Montellano, P. R. J. Am. Chem. Soc. 1966, 88, 4750-4751.
20. (b) van Tamelen, E. E.; Willett, J. D.; Clayton, R. B.; Lord, K. E. J. Am. Chem. Soc. 1966, 88, 4752-4753.
21. (c) Vilotijevic, I.; Jamison, T. F. Angew. Chem., Int. Ed. 2009, 48, 5250-5281.
22. (d) Topczewski, J. J.; Callahan, M. P.; Neighbors, J. D.; Wiemer, D. F. J. Am. Chem. Soc. 2009, 131, 14630-14631.
23. (e) Neighbors, J. D.; Beutler, J. A.; Wiemer, D. F. J. Org. Chem. 2005, 10, 925-931.
24. (a) Nicolaou, K. C.; Prasad, C. V. C.; Somera, P. K.; Hwang, C. K. J. Am. Chem. Soc. 1989, 111, 5335-5340.
25. (b) Morimoto, Y.; Nishikawa, Y.; Ueba, C.; Tanaka, T. Aneew. Chem. 2006, 118, 824-826.
26. (c) Mori, Y.; Yaegashi, K.; Fumkawa, H. J. Am. Chem., Soc. 1996, 118, 8158-8159.
27. (d) Heffron, T. P.; Jamison, T. F. Org. Lett. 2003, 5, 2339-2342.
28. (a) Dai, L.-Z.; Qi, M.-J.; Shi, Y.-L; Liu, X.-G.; Shi, M. Org. Lett. 2007, 9, 3191-3194.
29. (b) Tarselli, M. A.; Zuccarello, J. L.; Lee, S. J.; Gagne, M. R. Org. Lett. 2009, 11, 3490-3492.
30. (a) Kwon, D. W.; Cho, M. S.; Kim, Y. H. Synlett 2003, 7, 959-962.
31. (b) Park, H. S.; Kwon, D. W.; Lee, K.; Kim, Y. H. Tetrahedron. Lett. 2008, 49, 1616-1618.
32. Odedra, A.; Lush, S.-F.; Lui, R.-S. J. Org. Chem. 2007, 72, 567-573.
33. (a) Albanese, D.; Landini, D.; Penso, M. Chem. Commun. 1999, 2095-2096.
34. (b) Albanese, D.; Landini, D.; Lupi, V.; Penso, M. Ind. Eng. Chem. 2003, 42, 680-686.
35. After the submission, of this paper for review, we became aware of the following report that appeared, online on December 24, 2009:Cleator, E.; Baxter, C. A.; O'Hagan, M.; O'Riordan, T. L C.; Sheen, F. J.; Stewart, G. W. Tetrahedron Lett. 2010, 1079-1082.
36. (a) Hromatka, O.; Binder, D.; Knollmüller, M. Monatsh. Chem. 1968, 99, 1062-1067.
37. (b) Hasegawa, K.; Hirooka, S. Bull. Soc. Chem. Jpn. 1972, 45, 525-528.
38. (a) Zhou, A.; Hanson, P. R. Org. Lett. 2008, 10, 2951-2954.
39. (b) Zhou, A.; Rayabarapu, D.; Hanson, P. R. Org. Lett. 2009, 11, 531-534.
40. Rolfe, A.; Young, K.; Volp, K.; Schoenen, F.; Neuenswander, B.; Lushington, G. H.; Hanson, P. R. J. Comb. Chem. 2009, 11, 732-738.
41. Conventional heating in an oil bath required 20-24 h at 150 °C to afford the desired product, although yields were on average 10-20% lower.
42. 2-Fluorobenzenesulfonamides bearing additional halogen functionality on the benzene ring were designed for diversification at a later stage in library format. No reduction in yield or reaction rates for the epoxide cascade protocol was observed, when these were not present in the starting material.
43. 1H NMR, indicating the TBDMS group was not removed, under the reaction conditions producing the corresponding free OH group.
44. (a) Zhang, M.; Vedantham, P.; Flyiin, D. L.; Hanson, P. R. J. Org. Chem. 2004, 69, 8340-8344.
45. (b) Rolfe, A.; Probst, D.; Volp, K. A.; Omar, L; Flynn, D.; Hanson, P. R. J. Org. Chem. 2008, 73, 8785-8790.