A dearomatizing, thionium ion cyclization for the synthesis of functionalized, azaspirocyclic cyclohexadienones

Organic Letters

Volumn 10, Issue 7, 2008, Pages 1441-1444

  Ovens, Caroline ^a   Martin, Nathaniel G ^b   Procter, David J ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXADIENONE; CYCLOHEXANE DERIVATIVE; HETEROCYCLIC COMPOUND; QUATERNARY AMMONIUM DERIVATIVE; SPIRO COMPOUND; THIOL DERIVATIVE; THIONIUM;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; CYCLIZATION; SYNTHESIS;

AZA COMPOUNDS; CYCLIZATION; CYCLOHEXANES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; QUATERNARY AMMONIUM COMPOUNDS; SPIRO COMPOUNDS; SULFHYDRYL COMPOUNDS;

EID: 45849102103     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8002095     Document Type: Article

References (36)

1. Pummerer, R. Chem. Ber. 1909, 42, 2282.
2. (a) Akai, S.; Kita, Y. Top. Curr. Chem. 2007, 274, 35.
3. (b) Feldman, K. S. Tetrahedron 2006, 62, 5003.
4. (c) Bur, S. K.; Padwa, A. Chem. Rev. 2004, 104, 2401.
5. (d) Padwa, A.; Danca, D. M.; Ginn, J. D.; Lynch, S. M. J. Braz. Chem. Soc. 2001, 12, 571.
6. (e) Padwa, A.; Waterson, A. G. Curr. Org. Chem. 2000, 4, 175.
7. (f) Padwa, A.; Gunn, D. E., Jr.; Osterhout, M. H. Synthesis 1997, 1353.
8. We describe these reactions as "Pummerer-type" processes to show their relationship to "Pummerer" reactions in which similar thionium ions are generated from sulfoxides. See ref. 2.
9. Miller, M.; Tsang, W.; Merritt, A.; Procter, D. J. Chem. Commun. 2007, 498.
10. (a) McAllister, L. A.; McCormick, R. A.; Brand, S.; Procter, D. J. Angew. Chem., Int. Ed. 2005, 44, 452.
11. (b) McCormick, R. A.; James, K. M.; Willetts, N.; Procter, D. J. QSAR Comb. Sci. 2006, 25, 709.
12. (c) McAllister, L. A.; McCormick, R. A.; James, K. M.; Brand, S.; Willetts, N.; Procter, D. J. Chem. Eur. J. 2007, 13, 1032.
13. (a) Saitoh, T.; Shikiya, K.; Horiguchi, Y.; Sano, T. Chem. Pharm. Bull. 2003, 51, 667.
14. (b) Hanaoka, M.; Hirasawa, T.; Cho, W. J.; Yasuda, S. Chem. Pharm. Bull. 2000, 48, 399.
15. Previously reported Pummerer spirocyclizations involve addition to indole derivatives. For selected examples, see: (a) Magnus, P.; Sear, N. L.; Kim, C. S.; Vicker, N. J. Org. Chem. 1992, 57, 70.
16. (b) Amat, M.; Bosch, J. J. Org. Chem. 1992, 57, 5792.
17. (c) Catena, J.; Valls, N.; Bosch, J.; Bonjoch, J. Tetrahedron Lett. 1994, 35, 4433.
18. (d) Feldman, K. S.; Vidulova, D. B.; Karatjas, A. G. J. Org. Chem. 2005, 70, 6429.
19. (e) Feldman, K. S.; Karatjas, A. G. Org. Lett. 2006, 8, 4137.
20. (a) Kazmierski, W. M.; Furfine, E.; Spaltenstein, A.; Wright, L. L. Biorg. Med. Chem. Lett. 2002, 12, 3431.
21. (b) Badger, A. M.; Schwartz, D. A.; Picker, D. H.; Dorman, J. W.; Bradley, F. C.; Cheeseman, E. N.; DiMartino, M. J.; Hanna, N.; Mirabelli, C. K. J. Med. Chem. 1990, 33, 2963.
22. (c) Makovec, F.; Peris, W.; Revel, L.; Giovanetti, R.; Mennuni, L.; Rovati, L. C. J. Med. Chem. 1992, 35, 28.
23. (d) Sandmeier, P.; Tamm, C. Helv. Chim. Acta 1989, 72, 784.
24. (e) Yang, Y.; Chang, F.; Wu, Y. Helv. Chim. Acta 2004, 87, 1392.
25. (f) Sánchez, V.; Ahond, A.; Guilhem, J.; Poupat, C.; Potier, P. Bull. Soc. Chim. Fr. 1987, 877.
26. (a) Rishton, G. M.; Schwartz, M. A. Tetrahedron Lett. 1988, 29, 2643.
27. (b) Wardrop, D. J.; Burge, M. S.; Zhang, W.; Ortíz, J. A. Tetrahedron Lett. 2003, 44, 2587.
28. (c) Pigge, F. C.; Coniglio, J. J.; Dalvi, R. J. Am. Chem. Soc. 2006, 128, 3498.
29. (d) Ibarra-Rivera, T. R.; Gámez-Montano, R.; Miranda, L. D. Chem. Commun. 2007, 3485.
30. Marx, M. A.; Grillot, A.-L.; Louer, C. T.; Beaver, K. A.; Bartlett, P. A. J. Am. Chem. Soc. 1997, 119, 6153. See also refs 4 and 5.
31. See supporting information for CCDC numbers.
32. The stereochemistry was determined by NOE studies on the major diastereoisomers of 21 and 22 and inferred for the remainder.
33. For recent reviews; see: (a) Curran, D. P. In Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; Wiley-VCH: Weinheim, 2004.
34. (b) Zhang, W. Tetrahedron 2003, 59, 4475.
35. DiPietro, D.; Borzilleri, R. M.; Weinreb, S. M. J. Org. Chem. 1994, 59, 5856.
36. Padwa, A.; Kuethe, J. T. J. Org. Chem. 1998, 63, 4256.