Straightforward access to a structurally diverse set of oxacyclic scaffolds through a four-component reaction

Angewandte Chemie - International Edition

Volumn 44, Issue 40, 2005, Pages 6521-6525

  Jiménez, Oscar ^a   De La Rosa, Guillermo ^a   Lavilla, Rodolfo ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Glycosides; Lewis acids; Multicomponent reactions; Oxygen heterocycles; Synthetic methods

Indexed keywords

AMINO ACIDS; COMBINATORIAL MATHEMATICS; CONDENSATION; REACTION KINETICS; SYNTHESIS (CHEMICAL);

GLYCOSIDES; LEWIS ACID; MULTICOMPONENT REACTION; OXYGEN HETEROCYCLES; SYNTHETIC METHODS;

CARBOXYLIC ACIDS;

EID: 27144508168     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200501548     Document Type: Article

References (50)

1. For an overview of MCRs, see: a) Multicomponent Reactions (Eds.: J. Zhu, H. Bienaymé), Wiley-VCH, Weinheim, 2005.
2. For recent reviews, see: b) D. J. Ramón, M. Yus, Angew. Chem. 2005, 117, 1628;
3. Angew. Chem. Int. Ed. 2005, 44, 1602;
4. c) C. Simon, T. Constantieux, J. Rodriguez, Eur. J. Org. Chem. 2004, 4957;
5. d) R. V. A. Orru, M. de Greef, Synthesis 2003, 10, 1471;
6. e) J. Zhu, Eur. J. Org. Chem. 2003, 1133;
7. f) H, Bienaymé, C. Hulme, G. Oddon, P. Schmitt, Chem. Eur. J. 2000, 6, 3321;
8. g) A. Dömling, I. Ugi, Angew. Chem. 2000, 112, 3300;
9. Angew. Chem. Int. Ed. 2000, 39, 3168.
10. M. D. Burke, S. L. Schreiber, Angew. Chem. 2004, 116, 48;
11. Angew. Chem. Int. Ed. 2004, 43, 46.
12. a) F. Schweizer, Angew. Chem. 2002, 114, 240;
13. Angew. Chem. Int. Ed. 2002, 41, 230;
14. b) S. A. W. Gruner, E. Locardi, E. Lohof, H. Kessler, Chem. Rev. 2002, 102, 491.
15. a) L. S. Povarov, Russ. Chem. Rev. 1967, 36, 656;
16. b) K. A. Jorgensen, Angew. Chem. 2000, 112, 3702;
17. Angew. Chem. Int. Ed. 2000, 39, 3558;
18. c) S. Kobayashi, R. Akiyama, H. Kitagawa, J. Comb. Chem. 2001, 3, 196;
19. d) I. Carranco, J. L. Díaz, O. Jiménez, M. Vendrell, F. Albericio, M. Royo, R. Lavilla, J. Comb. Chem. 2005, 7, 33, and references therein.
20. a) V. Lucchini, M. Prato, G. Scorrano, M. Stivanello, G. Valle, J. Chem. Soc. Perkin Trans. 2 1992, 259;
21. b) S. Hermitage, D. A. Jay, A. Whiting, Tetrahedron Lett. 2002, 43, 9633;
22. c) R. Lavilla, M. C. Bernabeu, I. Carranco, J. L. Díaz, Org. Lett. 2003, 5, 717;
23. d) S. Kobayashi, R. Matsubara, Y. Nakamura, H. Kitagawa, M. Sugiura, J. Am. Chem. Soc. 2003, 125, 2507.
24. Very recently, multistep syntheses of similar compounds have been described; see: a) A. K. Ghosh, C.-X. Xu, S. S. Kulkarni, D. Wink, Org. Lett. 2005, 7, 7;
25. b) T. Sommermann, B. G. Kim, K. Peters, E.-M. Peters, T. Linker, Chem. Commun. 2004, 22, 2624;
26. c) P. R. Sridhar, K. C. Ashalu, S. Chandrasekaran, Org. Lett. 2004, 6, 1777.
27. Only two compounds of this type have been described in the literature as by-products in low-yielding Povarov-type reactions; see: a) R. Baudelle, P. Melnyk, B. Déprez, A. Tartar, Tetrahedron 1998, 54, 4125;
28. and b) Ref. [5a].
29. W. J. N. Meester, J. H. van Maarseveen, H. E. Schoemaker, H. Hiemstra, F. P. J. T. Rutjes, Eur. J. Org. Chem. 2003, 2519.
30. S. Kobayashi in Lewis Acids in Organic Synthesis, Vol. 2 (Ed.: H. Yamamoto), Wiley-VCH, Weinheim, 2000, p. 883.
31. For related processes, see: a) A. K. Ghosh, R. Kawahama, D. Wink, Tetrahedron Lett. 2000, 41, 8425;
32. b) A. K. Ghosh, R. Kawahama, Tetrahedron Lett. 1999, 40, 4751.
33. The minor isomer in these series is the epimer at the N-substituted stereogenic center.
34. T. Mukaiyama, Angew. Chem. 1979, 91, 798;
35. Angew. Chem. Int. Ed. Engt. 1979, 18, 707.
36. Aldehydes with α-hydrogen atoms were not included in this study.
37. In these series, protected (isopropylidene) D-ribonolactone and D-galactose derivatives were efficiently used as terminators, and the corresponding adducts were obtained with good conversions as mixtures of diastereomers.
38. For brevicomin-related derivatives, see: V. I. Tyvorskii, D. A. Astashko, O. G. Kulinkovich, Tetrahedron 2004, 60, 1473.
39. Experiments run at higher temperatures resulted in very complex mixtures.
40. For recent results, see: a) J. S. Yadav, B. V. S. Reddy, K. V. Rao, K. S. Raj, A. R. Prasad, S. K. Kumar, A. C. Kunwar, P. Jayaprakash, B. Jagannath, Angew. Chem. 2003, 115, 5356;
41. Angew. Chem. Int. Ed. 2003, 42, 5198;
42. b) S. K. Das, K. A. Reddy, J. Roy, Synlett 2003, 11, 1607;
43. c) R. A. Batey, D. A. Powell, A. Acton, A. J. Lough, Tetrahedron Lett. 2001, 42, 7935;
44. d) J. Zhang, C.-J. Li, J. Org. Chem. 2002, 67, 3969.
45. To our knowledge, this is the first example of Povarov-type reaction with glycals.
46. I. Arai, G. D. Daves, Jr., J. Org. Chem. 1979, 44, 21.
47. R. I. Longley, W. S. Emerson, J. Am. Chem. Soc. 1950, 72, 3079.
48. E. Borrione, M. Prato, G. Scorrano, M. Stivanello, V. Lucchini, J. Heterocycl. Chem. 1988, 25, 1831.
49. Studies directed toward the improvement of the stereoselectivity of the process are underway; we are currently evaluating the role of additives and ligands in these reactions.
50. Note added in proof: Dihydrofurans react in this MCR following similar trends to dihydropyrans; for examples, see the Supporting Information.