[8+2]formal cycloaddition reactions of tropones with azlactones under brønsted acid catalysis and synthesis of α-(2-tropyl), α-alkyl α-amino acids

European Journal of Organic Chemistry

Volumn 2014, Issue 7, 2014, Pages 1395-1400

  Esteban, Francisco ^a   Alfaro, Ricardo ^a   Yuste, Francisco ^a   Parra, Alejandro ^a   Ruano, José Luis García ^a   Alemán, José ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

Amino acids; Br nsted acids catalysis; Cycloaddition; Heterocycles; Tropones

Indexed keywords

EID: 84894426840     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201301774     Document Type: Article

References (39)

1. F. Pietra, Chem. Rev. 1973, 73, 293.
2. S. Ito, Y. Fujise, in: Topics in Nonbenzenoid Aromatic Chemistry (Eds.:, T. Nozoe, R. Breslow, K. Hafner, S. Ito, I. Murata), Hirokawa, Tokyo, 1977, vol. 2, p. 91.
3. F. Pietra, Acc. Chem. Res. 1979, 12, 132.
4. D. Lloyd, in: Nonbenzenoid Conjugated Carbocyclic Compounds, Elsevier, Amsterdam, 1984; pp 89-125, p. 126-132.
5. T. Asao, M. Oda, in: Methoden der Organischen Chemie (Houben-Weyl) (Ed.:, M. Regitz), Thieme, Stuttgart, Germany, 1985, vol. 5/2c, p. 710.
6. J. H. Rigby, in: Studies in Natural Products Chemistry, Stereoselective Synthesis Elsevier, Amsterdam, 1988, part A, vol. 1, p. 545.
7. A. E. Greene, M. A. Teixeria, E. Barreiro, A. Cruz, P. Crabbe, J. Org. Chem. 1982, 47, 2553.
8. B. M. Trost, P. R. Seoane, J. Am. Chem. Soc. 1987, 109, 615.
9. R. L. Funk, G. L. Bolton, J. Org. Chem. 1987, 52, 3174.
10. K. S. Feldman, J. H. Come, B. J. Kosmider, P. M. Smith, D. P. Rotella, M.-J. Wu, J. Org. Chem. 1989, 54, 92.
11. J. H. Rigby, H. S. Ateeq, J. Am. Chem. Soc. 1990, 112, 6442.
12. K. S. Feldman, M.-J. Wu, D. P. Rotella, J. Am. Chem. Soc. 1989, 111, 6457.
13. T. Graening, V. Bette, J. Neudorfl, J. Lex, H.-G. Schmalz, Org. Lett. 2005, 7, 4317.
14. L. Isakovic, J. A. Ashenhurst, J. L. Gleason, Org. Lett. 2001, 3, 4189.
15. P. Li, H. Yamamoto, J. Am. Chem. Soc. 2009, 131, 16628.
16. Y. Coquerel, J. P. Deprés, A. E. Greene, J. Philouze, J. Organomet. Chem. 2002, 659, 176.
17. J. H. Rigby, V. Sainte Claire, Synth. Commun. 2012, 25, 4115.
18. K. Kumar, A. Kapur, M. P. S. Ishar, Org. Lett. 2000, 2, 787.
19. M. Oda, A. Sugiyama, R. Takeuchi, Y. Fujiwara, R. Miyatake, T. Abe, S. Kuroda, Eur. J. Org. Chem. 2012, 2231, and references cited therein.
20. B. M. Trost, P. J. McDougall, O. Hartmann, P. T. Walhen, J. Am. Chem. Soc. 2008, 130, 14960.
21. Y. Du, J. Feng, X. Lu, Org. Lett. 2005, 7, 1987.
22. In a similar way, ketene aminals, formed in reactions of heterocyclic carbenes with conjugated aldehydes, react with tropones to yield bicyclic δ-lactones, presumably by an [8+3] annulation pathway, see:, V. Nair, M. Poonoth, S. Vellalath, E. Suresh, R. Thirumalai, J. Org. Chem. 2006, 71, 8964.
23. K. G. Jastrzabek, R. Subiros-Funosas, F. Albericio, B. Kolesinska, Z. J. Kaminski, J. Org. Chem. 2011, 76, 4506.
24. A. R. Katritzky, E. Todadze, P. Angrish, B. Draghici, J. Org. Chem. 2007, 72, 5794.
25. Y. Ohfune, T. Shinada, Eur. J. Org. Chem. 2005, 5127.
26. M. Tanaka, Chem. Pharm. Bull. 2007, 55, 349.
27. H. Vogt, S. Bräse, Org. Biomol. Chem. 2007, 5, 406; for other related reviews, see
28. C. Nájera, J. M. Sansano, Chem. Rev. 2007, 107, 4584.
29. K. Undheim, Amino Acids 2008, 34, 357.
30. J. Clayden, M. Donnard, J. Lefranc, D. J. Tetlow, Chem. Commun. 2011, 47, 4624.
31. A.-N. R. Alba, R. Rios, Chem. Asian J. 2011, 6, 720.
32. J. S. Fisk, R. A. Mosey, J. J. Tepe, Chem. Soc. Rev. 2007, 36, 1432.
33. R. A. Mosey, J. S. Fisk, J. J. Tepe, Tetrahedron: Asymmetry 2008, 19, 2755. For pioneering work in the organocatalytic field, see
34. J. Alemán, A. Milelli, S. Cabrera, E. Reyes, K. J. Jørgensen, Chem. Eur. J. 2008, 14, 10958.
35. S. Cabrera, E. Reyes, J. Alemán, A. Milelli, S. Kobbelgaard, K. A. Jørgensen, J. Am. Chem. Soc. 2008, 130, 12031. For an excellent recent paper, see
36. D. Uraguchi, Y. Ueki, A. Sugiyama, T. Ooi, Chem. Sci. 2013, 4, 1308.
37. CCDC-913779 (for 3Aa) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
38. CCDC-947015 (for 3Ba) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
39. S. A. Shaw, P. Aleman, J. Christy, J. W. Kampf, P. Va, E. Vedejs, J. Am. Chem. Soc. 2006, 128, 925