Unusual totally selective cyclodimerization of epoxides: Synthesis of a pair of diastereoisomers of enantiopure 2,5-disubstituted-1,4-dioxanes with C2 symmetry

Advanced Synthesis and Catalysis

Volumn 350, Issue 3, 2008, Pages 477-481

  Concellón, José M ^a   Bernad, Pablo L ^a   Del Solar, Virginia ^a   García Granda, Santiago ^a   Díaz, M Rosario ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Amino epoxides; Diastereoselectivity; Dimerization; Dioxanes; Enantiopurity

Indexed keywords

EID: 53849129569     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200700486     Document Type: Article

References (47)

1. Reviews on the synthesis and synthetic applications of epoxides: a) D. M. Hodgson, P. G. Humphreys, S. P. Hughes, Pure Appl. Chem. 2007, 79, 269-279;
2. b) E. M. Mcgarrigle, D. G. Gilheany, Chem. Rev. 2005, 105, 1563-1602;
3. c) V. K. Aggarwal, C. L. Winn, Acc. Chem. Res. 2004, 37, 611-620;
4. d) R. A. Sheldon, Applied Homogeneous Catalysis with Organometallic Compounds, Wiley-VCH, Weinheim, 2002;
5. e) L. A. Campbell, T. Kodadek, J. Mol. Catal. A: Chemical 1996, 113, 293-310;
6. f) D. Schinzer, Organic Synthesis Highlights II, Wiley-VCH, Weinheim, 1996;
7. g) G. A. Barf, R. A. Sheldon, J. Mol. Catal. A: Chemical 1995, 102, 23-39;
8. h) J. P. Collman, X. Zhang, V. J. Lee, E. S. Uffelman, J. I. Brauman, Science 1993, 261, 1404-1411.
9. I. Takekawa, H. Nukata, H. Nakamura, M. Miyamoto, Japanese Patent 10,265,564, 1998; Chem. Abstr. 1998, 129, 337617.
10. J. Conrad, U. A. Schaper, K. Bruns, German Patent 2,629,000, 1978; Chem. Abstr. 1978, 89, 80129.
11. W. Himmele, H. Mueller-Tamm, D. Wolff, A. Hofmann, German Patent 1,961,365, 1969; Chem. Abstr. 1971, 75, 77766.
12. F. Karrer, European Patent 88-810011, 1988; Chem. Abstr. 1978, 109, 190402.
13. J. D. McClure, US Patent 19,630,313, 1964; Chem. Abstr. 1964, 61, 47918.
14. a) H. Y. Kim, R. J. Kuhn, C. Patkar, R. Warrier, M. Cushman, Bioorg. Med. Chem. 2007, 15, 2667-2679;
15. b) J. A. L. Simond, A. J. C. Monteil, P. Carlier, French Patent 2,547,582, 1984; Chem. Abstr. 1985, 103, 54086.
16. J. Y. Lee, Y. K. Park, S. H. Seo, B. S. Yang, H. Park, Y. S. Lee, Arch. Pharm. 2002, 335, 487-494.
17. A. M. Verkatesan, World Patent 9,829,405, 1998; Chem. Abstr. 1998, 129, 109091.
18. a) K. Baum, J. Am. Chem. Soc. 1968, 90, 7083-7089;
19. b) H. Sugimoto, D. T. Sawyer, J. Org. Chem. 1985, 50, 1784-1786;
20. c) A. Braun, L. Toupet, J.-P. Lellouche, J. Org. Chem. 1996, 61, 1914-1915;
21. d) R. Martínez, M. Velasco, I. Martínez, I. Menconi, A. Ramírez, E. Angeles, I. Regla, R. López, J. Heterocyclic Chem. 1997, 34, 1865-1866;
22. e) L. Weber, M. Barlmeyer, J.-M. Quasdorff, H. L. Sievers, H.-G. Stammler, B. Neumann, Organometallics 1999, 18, 2497-2504.
23. M. Tiecco, L. Testaferri, F. Marini, S. Sternativo, C. Santi, L. Bagnoli, A. Temperini, Tetrahedron: Asymmetry 2003, 14, 1095-1102.
24. K. S. Kim, J. II Park, P. Ding, Tetrahedron Lett. 1998, 39, 6471-6474.
25. M. C. Wilkinson, R. Bell, R. Landon, P. O. Nikiforov, A. J. Walker, Synlett 2006, 2151-2153.
26. G. Pandey, A. L. Gaikwad, S. R. Gadre, Tetrahedron Lett. 2006, 47, 701-703.
27. H. Fujioka, N. Matsunaga, H. Kitagawa, Y. Nagatomi, M. Kondo, Y. Kita, Tetrahedron: Asymmetry 1995, 6, 2117-2120;
28. H. Fujioka, N. Matsunaga, H. Kitagawa, Y. Nagatomi, M. Kondo, Y. Kita, Tetrahedron: Asymmetry 1995, 6, 2113-2116.
29. J. Aubé, C. J. Mossman, S. Dickey, Tetrahedron 1992, 48, 9819-9826.
30. 2 symmetry: a) M. Vrettou, A. A. Gray, A. R. E. Brewer, A. G. M. Barrett, Tetrahedron 2007, 63, 1487-1536;
31. b) K. C. Bhowmick, N. N. Joshi, Tetrahedron: Asymmetry 2006, 17, 1901-1929;
32. c) G. Desimoni, G. Faita, K. A. Jorgensen, Chem. Rev. 2006, 106, 3561-3651;
33. d) S. Castrillón, C. Claver, Y. Diaz, Chem. Soc. Rev. 2005, 34, 702-713;
34. e) B. Delouvrie, L. Fensterbank, F. Najera, M. Malacria, Eur. J. Org. Chem. 2002, 67, 3507-3525;
35. f) A. K. Ghosh, P. Mathivanan, J.; Cappiello, Tetrahedron: Asymmetry 1998, 9, 1-45.
36. a) J. Barluenga, B. Baragaña, A. Alonso, J. M. Concellón, J. Chem. Soc., Chem. Commun. 1994, 969-970;
37. b) J. Barluenga, B. Baragaña, J. M. Concellón, J. Org. Chem. 1995, 60, 6696-6699.
38. J. M. Concellón, J. R. Suárez, S. García-Granda, M. R. Díaz, Org. Lett. 2005, 7, 247-250.
39. J. M. Concellón, J. R. Suárez, V. del Solar, J. Org. Chem. 2005, 70, 7447-7450.
40. J. M. Concellón, J. R. Suárez, V. del Solar, R. Llavona, J. Org. Chem. 2005, 70, 10348-10353.
41. J. M. Concellón, P. L. Bernad, V. del Solar, J. R. Suárez, S. García-Granda, M. R. Díaz, J Org Chem. 2006, 71, 6420-6426.
42. J. M. Concellón, V. del Solar, J. R. Suárez, E. G. Blanco, Tetrahedron 2007, 63, 2805-2810.
43. CCDC 654081 (1b) contains the supplementary crystallographic data for this paper. They can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif (or the Cambridge Data Centre, 12, Union Road. Cambridge CB21EZ, UK: fax: (+44)-1223-336-033; or deposit@ccdc.cam.ac.uk.
44. For clarity, only some relevant atoms are labelled.
45. [18].
46. 2NH, could support the existence of this equilibrium, due to the coordination of a tertiary amine with a Lewis acid is most difficult than a secondary amine.
47. A ring-opening of aziridinium 6 at C-3·could be also possible. However the obtained intermediate would allow access to a 7-membered cycle, which it is disfavoured with respect to the formation of the 6-membered cycle such as dioxane. So, the hypothetical formation of this intermediate would be reversible and it would be newly transformed into intermediates 6 and 7.