Stereoselective quaternary center construction via atom-transfer radical cyclization using silicon tethers on acyclic precursors

Organic Letters

Volumn 11, Issue 14, 2009, Pages 3148-3151

  Duplessis, Martin ^a,b   Waltzy, Marie Eve ^a,b   Bencheqroun, Mohammed ^a   Cardinal David, Benoit ^a,b   Guindon, Yvan ^a,b,c  

^a CLIN RESEARCH INSTITUTE OF MONTREAL   (Canada)

^b UNIVERSITÉ DE MONTRÉAL   (Canada)

^c MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; SILICON; VINYL DERIVATIVE;

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

ALLYL COMPOUNDS; CYCLIZATION; MOLECULAR STRUCTURE; SILICON; STEREOISOMERISM; VINYL COMPOUNDS;

EID: 67650293064     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901126y     Document Type: Article

References (52)

1. For reviews, see: (a) Fuji, K. Chem. Rev. 1993, 93, 2037.
2. (b) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 110, 402.
3. (c) Christoffers, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591.
4. (d) Denissova, I.; Barriault, L. Tetrahedron 2003, 59, 10105.
5. (e) Douglas, C. J.; Overman, L. E. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5363.
6. (f) Peterson, E. A.; Overman, L. E. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 11943.
7. (a) Fräter, G. Helv. Chim. Acta 1979, 62, 2825.
8. (b) Fräter, G.; Mueller, U.; Guenther, W. Tetrahedron 1984, 40, 1269.
9. Ohno, H.; Hiramatsu, K.; Tanaka, T. Tetrahedron Lett. 2004, 45, 75.
10. (a) Burke, E. D.; Gleason, J. L. Org. Lett. 2004, 6, 405.
11. (b) Arpin, A.; Manthorpe, J. M.; Gleason, J. L. Org. Lett. 2006, 8, 1359.
12. Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis; Christoffers, J., Baro, A., Eds.; Wiley-VCH: Weinheim, 2005.
13. Denmark, S. E.; Wilson, T. W.; Burke, M. T.; Heemstra, J. R., Jr. J. Am. Chem. Soc. 2007, 129, 14864.
14. (a) Cardinal-David, B.; Guérin, B.; Guindon, Y. J. Org. Chem. 2005, 70, 776.
15. (b) Cardinal-David, B.; Brazeau, J.-F.; Katsoulis, I.; Guindon, Y. Curr. Org. Chem. 2006, 10, 1939.
16. For use of allylsilane reagent, see: (a) Guindon, Y.; Guérin, B.; Chabot, C.; Ogilvie, W. W. J. Am. Chem. Soc. 1996, 118, 12528.
17. (b) For use of allyltin reagent, see: Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W.; Guindon, Y. Can. J. Chem. 2000, 78, 852.
18. (a) Guindon, Y.; Lavallée, J.-F.; Boisvert, L.; Chabot, C.; Delorme, D.; Yoakim, C.; Hall, D.; Lemieux, R.; Simoneau, B. Tetrahedron Lett. 1991, 32, 27.
19. (b) Guindon, Y.; Jung, G.; Guérin, B.; Ogilvie, W. W. Synlett 1998, 213.
20. (c) Brazeau, J.-F.; Mochirian, P.; Prévost, M.; Guindon, Y. J. Org. Chem. 2009, 74, 64.
21. (a) Giese, B.; Bulliard, M.; Wetterich, F.; Zeitz, H. G.; Rancourt, J.; Guindon, Y. Tetrahedron Lett. 1993, 34, 5885.
22. (b) Guindon, Y.; Benchequroun, M.; Bouzide, A. J. Am. Chem. Soc. 2005, 127, 554.
23. 2 = H, the ratio obtained was 6:1. The secondary hydroxyl group had to be protected in this case in a borinate and a monodentate Lewis acid used to activate the ester. (Cardinal-David B. Ph.D. Thesis, Université de Montréal, 2008).
24. See, for example: (a) Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Am. Chem. Soc. 1984, 49, 2298.
25. (b) Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500.
26. (c) Bogen, S.; Malacria, M. J. Am. Chem. Soc. 1996, 118, 3992.
27. (d) Fensterbank, L.; Dhimane, A.-L.; Wu, S.; Lacôte, E.; Bogen, S.; Malacria, M. Tetrahedron 1996, 11405, and references therein.
28. (e) Blaszykowski, C.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. Org. Lett. 2003, 8, 1341.
29. Allyl: (a) Shuto, S.; Terauchi, M.; Yahiro, Y.; Abe, H.; Ichikawa, S.; Matsuda, A. Tetrahedron Lett. 2000, 41, 4151.
30. (b) Kanazaki, M.; Ueno, Y.; Shuto, S.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 2422.
31. (c) Terauchi, M.; Yahiro, Y.; Abe, H.; Ichikawa, S.; Tovey, S. C.; Dedos, S. G.; Taylor, C. W.; Potter, B. V. L.; Matsuda, A.; Shuto, S. Tetrahedron 2005, 61, 3697.
32. (d) Shuto, S.; Yahiro, Y.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 2000, 65, 5547.
33. (e) Kodama, T.; Shuto, S.; Nomura, M.; Matsuda, A. Chem.-Eur. J. 2001, 7, 2332.
34. (f) Sakaguchi, N.; Hirano, S.; Matsuda, A.; Shuto, S. Org. Lett. 2006, 8, 3291.
35. (g) Stork, G.; Suk, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054.
36. (h) Xi, Z.; Rong, J.; Chattopadhyaya, J. Tetrahedron 1994, 50, 5255.
37. (i) Sukeda, M.; Ichikawa, S.; Matsuda, A.; Shuto, S. Angew. Chem., Int. Ed. 2002, 41, 4748.
38. (j) Sukeda, M.; Ichikawa, S.; Matsuda, A.; Shuto, S. J. Org. Chem. 2003, 68, 3465.
39. Curran, D. P.; Ramamoorthy, P. S. Tetrahedron 1993, 49, 4841.
40. (a) Baldwin, J. E. J. Chem. Soc, Chem. Commun. 1976, 734.
41. (b) Beckwith, A. L. J.; Easton, C. J.; Serelis, A. K. J. Chem. Soc., Chem. Commun. 1980, 482.
42. (a) Wilt, J. W.; Lusztyk, J.; Peeran, M.; Ingold, K. U. J. Am. Chem. Soc. 1988, 110, 281.
43. (b) Saigo, K.; Tateishi, K.; Hiroshi, A.; Saotome, Y. J. Org. Chem. 1988, 53, 1572.
44. Barton, T. J.; Revis, A. J. Am. Chem. Soc. 1984, 106, 3802.
45. For references on the β-silicon effect (also called silicon hyperconjugation), see: (a) Ibrahim, M. R.; Jorgensen, W. L. J. Am. Chem. Soc. 1989, 111, 819.
46. (b) Lambert, J. B.; Zhao, Y.; Emblidge, R. W.; Salvador, L. A.; Liu, X.; So, J.-H.; Chelius, E. C. Acc. Chem. Res. 1999, 32, 183.
47. (c) Chabaud, L.; James, P.; Landais, Y. Eur. J. Org. Chem. 2004, 3173.
48. Mochirian, P.; Cardinal-David, B.; Guérin, B.; Prévost, M.; Guindon, Y. Tetrahedron Lett. 2002, 43, 7067.
49. The optimization of this reaction was initially performed in benzene to avoid benzylic bromination. However, few reactions done in toluene demonstrate that good yields and excellent diastereoselectivites can be obtained which represent a great alternative to benzene (entries 1, 4, 5, 7, and 8 in Table 1 and entry 2 in Table 2).
50. The cyclic intermediates are unstable on silica. The allylated or vinylated products were observed in these cases.
51. See the Supporting Information.
52. See the Supporting Information for more details on the proof of structure of intermediates 48, 50, and 52a,b.