Brønsted acid-catalyzed three-component hosomi-sakurai reactions

Advanced Synthesis and Catalysis

Volumn 350, Issue 7-8, 2008, Pages 962-966

  Kampen, Daniela ^a   Ladépêche, Arnaud ^a   Claßen, Gerrit ^a   Lista, Benjamin ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Allylation; Br sted acids; Homoallylic ethers; Hosomi sakurai reaction; Multicomponent reactions; Organocatalysis

Indexed keywords

EID: 52149105532     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800036     Document Type: Article

References (45)

1. a) T. Jacques, I. E. Markó, J. Pospíšil, in: Multicomponent Reactions, Vol. 1, (Eds.: J. Zhu, H. Bienaymé), Wiley-VCH, Weinheim, 2005, pp. 398-452;
2. b) A. Hosomi, K. Miura, Bull. Chem. Soc. Jpn. 2004, 77, 835-851;
3. c) A. Hosomi, Acc. Chem. Res. 1988, 21, 200-206;
4. d) A. Hosomi, H. Sakurai, Tetrahedron Lett. 1976, 17, 1295-1298.
5. a) H. Sakurai, Pure Appl. Chem. 1982, 54, 1-22;
6. b) H. Sakurai, K. Sasaki, J. Hayashi, A. Hosomi, J. Org. Chem. 1984, 49, 2808-2809.
7. T. Mukaiyama, M. Ohshima, N. Miyoshi, Chem. Lett. 1987, 16, 1121-1124.
8. a) A. Mekhalfia, I. E. Markó, Tetrahedron Lett. 1991, 32, 4779-4782;
9. b) A. Mekhalfia, I. E. Markó, H. Adams, Tetrahedron Lett. 1991, 32, 4783-4786;
10. c) I. E. Markó, A. Mekhalfia, D. J. Bayston, H. Adams, J. Org. Chem. 1992, 57, 2211-2213;
11. d) M. El Gihani, H. Heaney, Synlett 1993, 433-434;
12. e) I. E. Markó, A. Mekhalfia, F. Murphy, D. J. Bayston, M. Bailey, Z. Janousek, S. Dolan, Pure Appl. Chem. 1997, 69, 565-570;
13. f) P. W. Anzalone, R. S. Mohan, Synthesis 2005, 2661-2663.
14. a) L. F. Tietze, A. Dölle, K. Schiemann, Angew. Chem. 1992, 104, 1366-1367;
15. Angew. Chem. Int. Ed. Engl. 1992, 31, 1372-1373;
16. b) J. S. Panek, J. Org. Chem. 1992, 57, 5790-5792;
17. c) L. F. Tietze, C. Wulff, C. Wegner, A. Schuffenhauer, K. Schiemann, J. Am. Chem. Soc. 1998, 120, 4276-4280;
18. d) J. Cossrow, S. D. Rychnovsky, Org. Lett. 2002, 4, 147-150.
19. B. H. Lipshutz, J. Burgess-Henry, G. P. Roth, Tetrahedron Lett. 1993, 34, 995-998.
20. M. W. Wang, Y. J. Chen, D. Wang, Synlett 2000, 385-387.
21. T. Watahiki, Y. Akabane, S. Mori, T. Oriyama, Org. Lett. 2003, 5, 3045-3048.
22. P. W. Anzalone, A. R. Baru, E. M. Danielson, P. D. Hayes, M. P. Nguyen, A. F. Panico, R. C. Smith, R. S. Mohan, J. Org. Chem. 2005, 70, 2091-2096.
23. M. J. Spafford, E. D. Anderson, J. R. Lacey, A. C. Palma, R. S. Mohan, Tetrahedron Lett. 2007, 48, 8665-8667.
24. [2b];
25. [5];
26. 2, see: M. Roux, M. Santelli, J.-L. Parrain, Org. Lett. 2000, 2, 1701-1704.
27. For intramolecular Sakurai reactions, see: a) M. Suginome, T. Iwanami, Y. Ito, J. Org. Chem. 1998, 63, 6096-6097;
28. b) W. R. Roush, G. J. Dilley, Synlett 2001, 955-959;
29. c) A. P. Dobbs, S. Martinović, Tetrahedron Lett. 2002, 43, 7055-7057;
30. d) S. Marumoto, J. J. Jaber, J. P. Vitale, S. D. Rychnovsky, Org. Lett. 2002, 4, 3919-3922;
31. e) K. Miura, R. Itaya, M. Horiike, H. Izumi, A. Hosomi, Synlett 2005, 3148-3150.
32. D. Kampen, B. List, Synlett 2006, 2589-2592.
33. [5c];
34. b) for the synthesis of homoallylic ethers from ketones in the presence of a mixture of TMSOTf and TfOH, see: L. F. Tietze, K. Schiemann, C. Wegner, J. Am. Chem. Soc. 1995, 117, 5851-5852.
35. For the synthesis of homoallylic ethers from ketones catalyzed by TfOH, see: a) L. F. Tietze, K. Schiemann, C. Wegner, C. Wulff, Chem. Eur. J. 1998, 4, 1862-1869;
36. b) L. F. Tietze, C. Wegner, C. Wulff, Eur. J. Org. Chem. 1998, 1639-1644;
37. c) L. F. Tietze, B. Weigand, L. Vökel, C. Wulff, C. Bittner, Chem. Eur. J. 2001, 7, 161-168;
38. d) L. F. Tietze, L. Vökel, C. Wulff, B. Weigand, C. Bittner, P. McGrath, K. Johnson, M. Schäfer, Chem. Eur. J. 2001, 7, 1304-1308;
39. e) L. F. Tietze, S. Hösken, J. Adrio, T. Kinzel, C. Wegner, Synthesis 2004, 2236-2239;
40. f) L. F. Tietze, T. Kinzel, S. Schmatz, J. Am. Chem. Soc. 2006, 128, 11483-11495.
41. For Brøsted acid-catalyzed Hosomi-Sakurai reactions of carbonyl compounds, see: a) K. Ishihara, A. Hasegawa, H. Yamamoto, Angew. Chem. 2001, 113, 4201-4203;
42. Angew. Chem. Int. Ed. 2001, 40, 4077-4079;
43. b) K. Ishihara, A. Hasegawa, H. Yamamoto, Synlett 2002, 1299-1301;
44. c) K. Ishihara, Y. Hiraiwa, H. Yamamoto, Synlett 2001, 1851-1854.
45. Chiral sulfonic acid 26 was prepared according to a modified procedure reported by Takahashi and Fukushi: K. Takahashi, K. Fukushi, Japanese Patent 132815, 2005.