Competing domino processes: Path-discriminating ability of epoxide stereochemistry at the angular position

Organic Letters

Volumn 11, Issue 16, 2009, Pages 3610-3613

  Aquino, Maurizio ^a   Safir, Imad ^a   Elkhayat, Zobida ^a   Gandara, Zoila ^a   Perez, Manuel ^a   Retailleau, Pascal ^a   Arseniyadis, Siméon ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; FUSED HETEROCYCLIC RINGS;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM;

BICYCLO COMPOUNDS, HETEROCYCLIC; COMBINATORIAL CHEMISTRY TECHNIQUES; EPOXY COMPOUNDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 68949086180     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9013377     Document Type: Article

References (27)

1. (a) Tietze, L. F. Chem. Rev. 1996, 96, 115-136.
2. (b) Domino Reactions In Organic Synthesis; Tietze, L. F., Brasche, G., Gericke, K. M., Eds.; Wiley-VCH: Weinheim, Germany, 2006; ISBN 3-527-29060-5.
3. Elkhayat, Z.; Safir, I.; Retailleau, P.; Arseniyadis, S. Org. Lett. 2007, 9, 4841-4844.
4. The first example of an intramolecular [4 + 2 + 2] cycloaddition was reported by Lautens et al.: Lautens, M.; Tam, W.; Lautens, J. C.; Edwards, L. G.; Crudden, C. M.; Smith, C. J. Am. Chem. Soc. 1995, 117, 6863-6879.
5. For recent examples, see: (a) Ozturk, C.; Topal, K.; Avijente, V.; Tuzun, N.; Sanchez, E.; Arseniyadis, S. J. Org. Chem. 2005, 70, 7080-7086.
6. (b) Safir, I.; Castellote, I.; Porcel, S.; Kaoudi, T.; Birlirakis, N.; Toupet, L.; Arseniyadis, S. Chem.-Eur. J. 2006, 12, 7337-7344.
7. (c) Elkhayat, Z.; Safir, I.; Castellote, I.; Retailleau, P.; Arseniyadis, S. Org. Lett. 2008, 10, 2219-2222.
8. (d) Elkhayat, Z.; Safir, I.; Aquino, M.; Perez, M.; Gandara, Z.; Retailleau, P.; Arseniyadis, S. Eur. J. Org. Chem. 2009, 2687-2694.
9. For an intermolecular serial process see: Wender, P. A.; Gamber, G. G.; Scanio, M. J. C. Angew. Chem., Int. Ed. 2001, 40, 3895-3897.
10. For reviews on the use of microwaves in organic synthesis see: (a) de la Hoz, A.; Diaz-Ortis, A.; Moreno, A.; Langa, F. Eur. J. Org. Chem. 2000, 3659-3673.
11. (b) Kappe, C. O.; Stadler, A. Microwaves in Organic and Medicinal Chemistry; Wiley-VCH: Weinheim, Germany, 2005.
12. (c) Kappe, C. O.; Dallinger, D. Drug Discovery 2006, 5, 51-63.
13. For articles dealing with specific aspects of organolead chemistry see: (a) Criegee, R. In Oxidation In Organic Chemistry; Wiberg, K. B., Ed.; Academic Press: New York, 1965; Part A, pp 277-366.
14. (b) Rubottom, G. M. In Oxidation In Organic Chemistry; Trahanovsky, W. H., Ed.; Academic Press: London, UK, 1982; Vol. D, Chapter 1.
15. (c) Moloney, M. G. Main Group Metal Chem. 2001, 24, 653-660.
16. For [m + n + o] cycloadditions, see: (a) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876-2877.
17. (b) Wegner, H. A.; de Meijere, A.; Wender, P. A. J. Am. Chem. Soc. 2005, 127, 6530-6531.
18. (c) Wender, P. A.; Christy, J. P. J. Am. Chem. Soc. 2006, 5354-5355, and references cited therein.
19. 2 or the solvent used (PhMe or AcOH).
20. For endo, exo mode discussion, see: (a) Fujiwara, K.; Murai, A. Bull. Chem. Soc. Jpn. 2004, 77, 2129-2146.
21. (b) Valentine, J. C.; McDonald, F. E. Synlett 2006, 1816-1828.
22. (c) Kumar, V. S.; Wan, S.; Aubele, D. L.; Floreancig, P. E. Tetrahedron: Asymmetry 2005, 16, 3570-3578.
23. For a computational study on bicyclic epoxonium ions, see: (d) Wan, S.; Gunaydin, H.; Houk, K. N.; Floreancig, P. E. J. Am. Chem. Soc. 2007, 129, 7915-7923.
24. We systematically elucidated the structures of the resulting domino products by extended high-field NMR studies, and corroborated by several single-crystal X-ray diffraction analyses and molecular mechanics calculations.
25. 2, but nothing useful was achieved.
26. Swain, C. G.; Powell, A. L.; Sheppard, W. A.; Morgan, C. H. J. Am. Chem. Soc. 1979, 101, 3576-3583.
27. From a more general point of view, the results obtained raise the question of "how the C11 stereochemistry can be controlled so as to control the formation of one type of product over another", as one of the referees has kindly remarked.