Boronated enynes as versatile sources of stereodefined and skeletally diverse molecules

Organic Letters

Volumn 9, Issue 9, 2007, Pages 1717-1720

  Hercouet, Alain ^a   Berrée, Fabienne ^a   Lin, Chia Hui ^a   Toupet, Loïc ^b   Carboni, Bertrand ^a  

^a Campus de Beaulieu ^*  (France)

^b UMR 6626   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BORON DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; ISOMERISM; STEREOISOMERISM; SYNTHESIS;

BORON COMPOUNDS; CATALYSIS; CYCLIZATION; ISOMERISM; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM;

EID: 34248395165     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070400s     Document Type: Article

References (38)

1. Schreiber, S. L Science 2000, 287, 1964. For a discussion of the use of DOS to explore biology,
2. see: Schreiber, S. L. Chem. Eng. News 2003, 81, 51.
3. Moulin, E.; Barluenga, S.; Totzke, F.; Winssinger, N. Chem. Eur. J. 2006, 12, 8819.
4. Adriaenssens, L. V.; Austin, C. A.; Gibson, M.; Smith, D.; Hartley, R. C. Eur. J. Org. Chem. 2006, 4998.
5. Fitzmaurice, R. J.; Etheridge, Z. C.; Jumel, E.; Woolfson, D. N.; Caddick, S. Chem. Commun. 2006, 4814.
6. Kotha, S.; Mandal, K.; Tiwari, A.; Mobin, S. M. Chem. Eur. J. 2006, 12, 8024.
7. Wyatt, E. E.; Fergus, S.; Galloway, W. R.; Bender, A.; Fox, D. J.; Plowright, A. T.; Jessiman, A. S.; Welch, M.; Spring, D. R. Chem. Commun. 2006, 3296.
8. Freifeld, I.; Holtz, E.; Dahmann, G.; Langer, P. Eur. J. Org. Chem. 2006, 3251.
9. Oikawa, M.; Naito, S.; Sasaki, M. Tetrahedron Lett. 2006, 47, 4763.
10. Lu, K.; Huang, M.; Xiang, Z.; Liu, Y.; Chen, J.; Yang, Z. Org. Lett. 2006, 8, 1193.
11. Burke, M. D.; Schreiber, S. L. Angew. Chem., Int. Ed. 2004, 43, 46.
12. For a recent and elegant application of this strategy, see: Kumagai, N.; Muncipito, G.; Schreiber, S. L. Angew. Chem., Int. Ed. 2006, 45, 3635.
13. (a) For a pioneering work, see: Vaultier, M.; Truchet, F.; Carboni, B.; Hoffmann, R. W.; Denne, I. Tetrahedron Lett. 1987, 28, 4169.
14. (b) For recent reviews, see: Hilt, G.; Bolze, P. Synthesis 2005, 2091.
15. Carboni, B.; Carreaux, F. In Boronic Acids; Hall, D. G., Ed.; Wiley-VCH: Weinheim, 2005; pp 343-376.
16. (c) See also more recently: Kim, M.; Lee, D. Org. Lett. 2005, 7, 1865.
17. De, S.; Welker, M. E. Org. Lett. 2005, 7, 2481.
18. Yamamoto, Y.; Ishii, J.-I.; Nishiyama, H.; Itoh, K. J. Am. Chem. Soc. 2005, 127, 9625.
19. Yamamoto, Y.; Hattori, K.; Ishii, J.; Nishiyama, H. Tetrahedron 2006, 62, 4294.
20. Hilt, G.; Hesse, W.; Harms, K. Org. Lett. 2006, 8, 3287.
21. Gao, X.; Hall, D.; Deligny, M.; Favre, A.; Carreaux, F.; Carboni, B. Chem. Eur. J. 2006, 12, 3132.
22. Berrée, F.; Debache, A.; Marsac, Y.; Collet, B.; Girard-Le Bleiz, P.; Carboni, B. Tetrahedron 2006, 62, 4027.
23. Debache, A.; Boumoud, B.; Amimour, M.; Belfaitah, A.; Rhouati, S.; Carboni, B. Tetrahedron Lett. 2006, 47, 5697.
24. For some reviews on cycloisomerization of enynes, see: Ma, S.; Yu, S.; Gu, Z. Angew. Chem., Int. Ed. 2006, 45, 200.
25. Bruneau, C. Angew. Chem., Int. Ed. 2005, 44, 2328.
26. Lloyd-Jones, G. C. Org. Biomol Chem. 2003, 1, 215.
27. Trost, B. M.; Frederiksen, M. U.; Rudd, M. T. Angew. Chem., Int. Ed. 2005, 44, 6630.
28. Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813.
29. Trost, B. M.; Toste, D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067.
30. Trost, B. M.; Dong, L.; Schroeder, G. M. J. J. Am. Chem. Soc. 2005, 127, 10259 and references therein.
31. Lombardo, M.; Morganti, S.; Tozzi, M.; Trombini, C. Eur. J. Org. Chem. 2002, 2823.
32. We have no explanation for this different behaviour, compared with other enynes. Such a protodeboronation is often associated with metal-catalyzed reactions of boronic acids. Only the boronated allylboronate 4 can react with the aldehyde, and the final product was easily separated from the non-boronated Diels-Alder cycloadduct.
33. This behaviour could be attributed to the presence of an electron-withdrawing group in position 2 of 2d that favors the dimerization process. See, for example: McIntosh, J. M.; Sieler, R. A. J. Org. Chem. 1978, 43, 4431.
34. See Supporting Information for X-ray cristallographic analysis of 5.
35. Zhang, A.; Kan, Y.; Jiang, B. Tetrahedron 2001, 57, 2305.
36. For other reports dealing with metal-eatalyzed synthesis of dienylboronic esters, see: ref 4c and Renaud, J.; Graf, C. D.; Oberer, L. Angew. Chem., Int. Ed. 2000, 39, 3101.
37. Micalizio, G. C.; Schreiber, S. L. Angew. Chem., Int. Ed. 2002, 41, 3272.
38. Fürstner, A.; Stelzer, F.; Szillat, H. J. J. Am. Chem. Soc. 2001, 123, 11863.