Cu(I)-NHC catalyzed Asymmetric Silyl transfer to unsaturated Lactams and Amides

Organic Letters

Volumn 16, Issue 2, 2014, Pages 476-479

  Pace, Vittorio ^a   Rae, James P ^a   Procter, David J ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84896762810     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol4033623     Document Type: Article

References (67)

1. Reviews: (a) Oestreich, M.; Hartmann, E.; Mewald, M. Chem. Rev. 2013, 113, 402.
2. Hartmann, E.; Vyas, D. J.; Oestreich, M. Chem. Commun. 2011, 7917.
3. Suginome, M.; Ito, Y. Chem. Rev. 2000, 100, 3221.
4. Hartmann, E.; Oestreich, M. Chim. Oggi 2011, 29, 34.
5. Ager, D. J.; Fleming, I. J. Chem. Soc., Chem. Commun. 1978, 177.
6. Fleming, I.; Henning, R.; Plaut, H. J. Chem. Soc., Chem. Commun. 1984, 29.
7. Fleming, I.; Sanderson, P. E. J. Tetrahedron Lett. 1987, 28, 4229.
8. Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1694.
9. Tamao, K.; Tanaka, T.; Nakajima, T.; Sumiya, R.; Arai, H.; Ito, Y. Tetrahedron Lett. 1986, 27, 3377. For selected reviews, see
10. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063.
11. Fleming, I. In Science of Synthesis; Fleming, I., Ed.; Thieme: Stuttgart, 2002; Vol. 4; pp 927-946.
12. Xu, L.-W.; Li, L.; Lai, G.-Q.; Jiang, J.-X. Chem. Soc. Rev. 2011, 40, 1777.
13. Iannazzo, L.; Molander, G. A. Eur. J. Org. Chem. 2012, 4923.
14. Lipshutz, B. H.; Sclafani, J. A.; Takanami, T. J. Am. Chem. Soc. 1998, 120, 4021.
15. Auer, G.; Weiner, B.; Oestreich, M. Synthesis 2006, 2113.
16. Ito, H.; Ishizuka, T.; Tateiwa, J.-i.; Sonoda, M.; Hosomi, A. J. Am. Chem. Soc. 1998, 120, 11196.
17. Clark, C. T.; Lake, J. F.; Scheidt, K. A. J. Am. Chem. Soc. 2004, 126, 84.
18. Oestreich, M.; Weiner, B. Synlett 2004, 2139.
19. Calderone, J. A.; Santos, W. L. Org. Lett. 2012, 14, 2090.
20. Xuan, Q.-Q.; Zhong, N.-J.; Ren, C.-L.; Liu, L.; Wang, D.; Chen, Y.-J.; Li, C.-J. J. Org. Chem. 2013, 78, 11076.
21. Matsumoto, Y.; Hayashi, T.; Ito, Y. Tetrahedron 1994, 50, 335.
22. Hayashi, T.; Matsumoto, Y.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 5579.
23. Reviews of Si-B chemistry: Ohmura, T.; Suginome, M. Bull. Chem. Soc. Jpn. 2009, 82, 29 and ref 1a.
24. Walter, C.; Auer, G.; Oestreich, M. Angew. Chem., Int. Ed. 2006, 45, 5675.
25. Walter, C.; Oestreich, M. Angew. Chem., Int. Ed. 2008, 47, 3818.
26. Walter, C.; Fröhlich, R.; Oestreich, M. Tetrahedron 2009, 65, 5513.
27. Hartmann, E.; Oestreich, M. Angew. Chem., Int. Ed. 2010, 49, 6195.
28. Hartmann, E.; Oestreich, M. Org. Lett. 2012, 14, 2406.
29. NHCs in metal catalysis: (a) Díez-González, S.; Marion, N.; Nolan, S. P. Chem. Rev. 2009, 109, 3612.
30. Díez-González, S.; Nolan, S. P. Aldrichimica Acta 2008, 41, 43.
31. Glorius, F. Topics in Organometallic Chemistry, N-Heterocyclic Carbenes in Transition Metal Catalysis; Springer-Verlag: Berlin, Heidelberg, 2006; Vol. 21, pp 1-218.
32. Lee, K.-S.; Hoveyda, A. H. J. Am. Chem. Soc. 2010, 132, 2898.
33. Lee, K.-S.; Wu, H.; Haeffner, F.; Hoveyda, A. H. Organometallics 2012, 31, 7823. Metal-free, NHC-catalyzed C-Si bond formation
34. O'Brien, J. M.; Hoveyda, A. H. J. Am. Chem. Soc. 2011, 133, 7712. For asymmetric allylic silylation using a Cu(I)-NHC system and PhMe2SiBpin
35. Delvos, L. B.; Vyas, D. J.; Oestreich, M. Angew. Chem., Int. Ed. 2013, 52, 4650.
36. Harb, H. Y.; Collins, K. D.; Altur, J. V. G.; Bowker, S.; Campbell, L.; Procter, D. J. Org. Lett. 2010, 12, 5446.
37. Pace, V.; Rae, J. P.; Harb, H. Y.; Procter, D. J. Chem. Commun. 2013, 49, 5150.
38. For alternative asymmetric approaches to β-silyl carbonyl compounds, see: (a) Ibrahem, I.; Santoro, S.; Himo, F.; Córdova, A. Adv. Synth. Catal. 2011, 353, 245.
39. Welle, A.; Petrignet, J.; Tinant, B.; Wouters, J.; Riant, O. Chem.-Eur. J. 2010, 16, 10980.
40. Lipshutz, B. H.; Tanaka, N.; Taft, B. R.; Lee, C.-T. Org. Lett. 2006, 8, 1963.
41. Shintani, R.; Okamoto, K.; Hayashi, T. Org. Lett. 2005, 7, 4757.
42. Kacprzynski, M. A.; Kazane, S. A.; May, T. L.; Hoveyda, A. H. Org. Lett. 2007, 9, 3187.
43. Cottet, P.; Müller, D.; Alexakis, A. Org. Lett. 2013, 15, 828. For selected examples of the use of α,β-unsaturated lactams in conjugate asymmetric additions with different nucleophiles, see
44. Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852 (arylboron reagents).
45. Gini, F.; Hessen, B.; Feringa, B. L.; Minnaard, A. J. Chem. Commun. 2007, 710 (arylsiloxanes).
46. Smith, A. J.; Abbott, L. K.; Martin, S. F. Org. Lett. 2009, 11, 4200 (2-heteroarylzinc reagents).
47. Jin, S.-S.; Wang, H.; Xu, M.-H. Chem. Commun. 2011, 72300
48. Pineschi, M.; Del Moro, F.; Gini, F.; Minnaard, A. J.; Feringa, B. L. Chem. Commun. 2004, 1244 (organozinc and organoaluminum reagents).
49. Fleming, I.; Reddy, N. L.; Takaki, K.; Ware, A. C. J. Chem. Soc., Chem. Commun. 1987, 1472.
50. Hagen, T. J. Synlett 1990, 63.
51. Silylzinc additions: Barrett, A. G. M.; Head, J.; Smith, M. L.; Stock, N. S.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1999, 64, 6005. See also ref 14a.
52. Auxiliary-controlled asymmetric silyl additions to α,β- unsaturated amides: (a) Crump, R. A. N. C.; Fleming, I.; Urch, C. J. J. Chem. Soc., Perkin Trans. 1 1994, 701.
53. Palomo, C.; Aizpurua, J. M.; Iturburu, M.; Urchegui, R. J. Org. Chem. 1994, 59, 240.
54. Fleming, I.; Jones, G. R.; Kindon, N. D.; Landais, Y.; Leslie, C. P.; Morgan, I. T.; Peukert, S.; Sarkar, A. K. J. Chem. Soc., Perkin Trans. 1 1996, 1171.
55. Fleming, I.; Mwaniki, J. M. J. Chem. Soc., Perkin Trans. 1 1998, 1237.
56. Ahmar, M.; Duyck, C.; Fleming, I. J. Chem. Soc., Perkin Trans. 1 1998, 2721.
57. Dambacher, J.; Bergdahl, M. J. Org. Chem. 2005, 70, 580.
58. For selected reviews, see: (a) Pace, V.; Hoyos, P.; Castoldi, L.; Domínguez de María, P.; Alcántara, A. R. ChemSusChem 2012, 5, 1369.
59. Aycock, D. F. Org. Process Res. Dev. 2007, 11, 156.
60. For an example of a nonasymmetric conjugate addition of organometallics (RLi and RMgX) to N-tosyl α,β-unsaturated amides, see: Nagashima, H.; Ozaki, N.; Washiyama, M.; ltoh, K. Tetrahedron Lett. 1985, 26, 657.
61. Miyamoto, S.; Mori, A. Neurosciences 1985, 11, 1.
62. Straightforward preparation of SmI2: (a) Szostak, M.; Spain, M.; Procter, D. J. J. Org. Chem. 2012, 77, 3049. N-Ts deprotection using the reagent
63. Knowles, H.; Parsons, A. F.; Pettifer, R. M. Synlett 1997, 271. Selected reviews on the use of SmI2 in organic synthesis
64. Procter, D. J.; Flowers, R. A., II; Skrydstrup, T. Organic Synthesis Using Samarium Diiodide: A Practical Guide; RSC Publishing: Cambridge, 2009.
65. Szostak, M.; Procter, D. J. Angew. Chem., Int. Ed. 2012, 51, 9238.
66. Szostak, M.; Spain, M.; Procter, D. J. Chem. Soc. Rev. 2013, 42, 9155.
67. Ferrarini, R. S.; Dos Santos, A. A.; Comasseto, J. V. Tetrahedron 2012, 68, 10601 and references cited therein. See also ref 2.