Reduction of olefins using ruthenium carbene catalysts and silanes

Synlett

Volumn , Issue 16, 2005, Pages 2449-2452

  Menozzi, Candice ^a   Dalko, Peter I ^a   Cossy, Janine ^a  

^a CNRS   (France)

Author keywords

Hydrosilylation; Reduction; Stereoselective synthesis

Indexed keywords

ALKENE DERIVATIVE; CARBENOID; RUTHENIUM DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CATALYST; CYCLIZATION; HYDROSILYLATION; REDUCTION; RING CLOSING METATHESIS; STEREOCHEMISTRY;

EID: 26844549548     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-872695     Document Type: Article

References (50)

1. References for selected reviews see: (a) Trnka, T. M. Acc. Chem. Res. 2001, 34, 18.
2. (b) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012.
3. (c) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565.
4. (d) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036.
5. (e) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199.
6. (f) Giessert, A. J.; Diver, S. T. Chem. Rev. 2004, 104, 1317.
7. (g) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1.
8. (h) Mori, M. In Handbook of Metathesis, Vol. 2; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003, 176.
9. (i) Connon, S. J.; Blechert, S. Angew. Chem. Int. Ed. 2003, 42, 1900.
10. (j) Schrock, R. R.; Hoveyda, A. H. Angew. Chem. Int. Ed. 2003, 42, 4592.
11. (k) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3013.
12. (l) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
13. (m) Astruc, D. New J. Chem. 2005, 29, 42.
14. (a) Alcaide, B.; Almendros, P. Chem.-Eur. J. 2003, 9, 1259.
15. (b) For non-metathetic transformations of organic substrates catalyzed by various ruthenium complexes, see: Trost, B. M.; Toste, D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067.
16. (c) See also: Ajamian, A.; Gleason, J. L. Angew. Chem. Int. Ed. 2004, 43, 3754.
17. (d) Review on the interface of ruthenium-carbene and ruthenium-hydride chemistry:
18. (e) Schmidt, B. Eur. J. Org. Chem. 2004, 1865.
19. Tallarico, J. A.; Malnick, L. A.; Snapper, M. L. J. Org. Chem. 1999, 64, 344.
20. Peppers, B. P.; Diver, S. T. J. Am. Chem. Soc. 2004, 126, 9524.
21. (a) Mori, M.; Saito, N.; Tanaka, D.; Takimoto, M.; Sato, Y. J. Am. Chem. Soc. 2003, 125, 5606.
22. (b) Quayle, P.; Fengas, D.; Richards, S. Synlett 2003, 1797.
23. For other non-metathetic activities of Ru carbene complexes see: (c) Schmidt, B. Angew. Chem. Int. Ed. 2003, 42, 4996.
24. (d) Faulkner, J.; Edlin, C. D.; Fengas, D.; Preece, I.; Quayle, P.; Richards, S. N. Tetrahedron Lett. 2005, 46, 2381.
25. (e) Edlin, C. D.; Faulkner, J.; Fengas, D.; Knight, C. K.; Parker, J.; Preece, I.; Quayle, P.; Richards, S. N. Synlett 2005, 572.
26. Lopez, F.; Delgado, A.; Rodriguez, J. R.; Castedo, L.; Mascarenas, J. L. J. Am. Chem. Soc. 2004, 126, 10262.
27. (a) Alcaide, B.; Almendros, P.; Alonso, J. M.; Aly, M. F. Org. Lett. 2001, 3, 3781.
28. (b) Cadot, C.; Dalko, P. I.; Cossy, J. Tetrahedron Lett. 2002, 43, 1839.
29. (c) Sutton, A. E.; Seigal, B. A.; Finnegan, D. F.; Snapper, M. L. J. Am. Chem. Soc. 2002, 124, 13390.
30. (d) Wipf, P.; Rector, S. R.; Takahashi, H. J. Am. Chem. Soc. 2002, 124, 14848.
31. (e) Schmidt, B. J. Org. Chem. 2004, 69, 7672.
32. (f) Le Notre, J.; Touzani, R.; Lavastre, O.; Bruneau, C.; Dixneuf, P. H. Adv. Synth. Catal. 2005, 347, 783.
33. (g) Bressy, C.; Menant, C.; Piva, O. Synlett 2005, 577.
34. (a) Maifeld, S. V.; Miller, R. L.; Lee, D. Tetrahedron Lett. 2002, 43, 6363.
35. Hydrosilylation of alkynes: (b) Aricó, C. S.; Cox, L. R. Org. Biomol. Chem. 2004, 2, 2558.
36. (c) Maifeld, S. V.; Tran, M. N.; Lee, D. Tetrahedron Lett. 2005, 46, 105.
37. (a) Louie, J.; Bielawski, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 11312.
38. (b) Cossy, J.; Bargiggia, F.; BouzBouz, S. Org. Lett. 2003, 5, 459.
39. For the use of silanes in selective reduction of olefins see: Jurkauskas, V.; Sadighi, J. P.; Buchwald, S. L. Org. Lett. 2003, 5, 2417 and references cited therein.
40. Product ratio was determined by GC-MS.
41. +], 267 (25), 173 (97), 135 (59), 115 (38), 107 (32), 103 (100), 75 (54), 69 (45).
42. Selected conjugate reductions using metal catalysts: (a) Mahoney, W. S.; Stryker, J. M. J. Am. Chem. Soc. 1989, 111, 8818.
43. (b) Lipshutz, B. H.; Keith, J.; Papa, P.; Vivian, R. Tetrahedron Lett. 1998, 39, 4627.
44. (c) Mori, A.; Fujita, A.; Kajiro, H.; Nishihara, Y.; Hiyama, T. Tetrahedron 1999, 55, 4573.
45. (d) Chiu, P.; Szeto, C.-P.; Geng, Z.; Cheng, K.-F. Org. Lett. 2001, 3, 1901.
46. (e) Lipshutz, B. H.; Papa, P. Angew. Chem. Int. Ed. 2002, 41, 4580.
47. (f) Ito, H.; Ishizuka, T.; Arimoto, K.; Miura, K.; Hosomi, A. Tetrahedron Lett. 1997, 38, 8887.
48. +], 121 (100).
49. 1H NMR spectra. Moreover, 28 was transformed to the known β-hydroxy ester (TBAF, overnight), and the spectral data of the desilylated compound was compared with the literature data: Bouzide, A. Org. Lett. 2002, 4, 1347.
50. As one of our referees pointed out, it is likely that hydrogenation occurred by the metathesis-inactive catalyst after the RCM reaction was completed, because the RCM was much faster than the modification of carbene catalyst by silanes or hydrogen, generated from dimerization of silanes.