Asymmetric synthesis of γ-siloxyenamides via chiral auxiliary-mediated diaseteroselective coupling of ynamides, aldehydes, and silane by nickel catalyst

Heterocycles

Volumn 82, Issue 2, 2010, Pages 1181-1187

  Saito, Nozomi ^a   Katayama, Tomoyuki ^a   Sato, Yoshihiro ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79952740646     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-10-S(E)122     Document Type: Article

References (22)

1. For recent reviews on chemistry of ynamides, see: (a) C. A. Zificsak, J. A. Mulder, R. P. Hsung, C. Rameshkumar, and L.-L. Wei, Tetrahedron, 2001, 57, 7575;
2. (b) J. A. Mulder, K. C. M. Kurtz, and R. P. Hsung, Synlett, 2003, 1379;
3. (c) 'Tetrahedron Symposia-in-Print No. 118' ed. by R. P. Hsung, Tetrahedron, 2006, 62, 3783;
4. (d) G. Evano, A. Coste, and K. Jouvin, Angew. Chem. Int. Ed., 2010, 49, 2840;
5. (e) K. A. DeKorver, H. Li, A. G. Lohse, R. Hayashi, Z. Lu, Y. Zhang, and R. P. Hsung, Chem. Rev, 2010, 110, 5064.
6. For our reports on transition metal catalysis based on ynamide as a platform, see: (a) N. Saito, Y. Sato, and M. Mori, Org. Lett, 2002, 4, 803;
7. (b) M. Mori, H. Wakamatsu, N. Saito, Y. Sato, R. Narita, Y. Sato, and R. Fujita, Tetrahedron, 2006, 62, 3872.
8. N. Saito, T. Katayama, and Y. Sato, Org. Lett, 2008, 10, 3829.
9. For recent examples of the preparation of γ-alkoxyenamide derivatives and their synthetic application, see: (a) H. McAlonan, J. P. Murphy, M. Nieuwenhuyzen, K. Reynolds, P. K. S. Sarma, P. J. Stevenson, and N. Thompson, J. Chem. Soc, Perkin Trans. 1, 2002, 69;
10. (b) P. M. Ylioja, A. D. Mosley, C. E. Charlot, and D. R. Carbery, Tetrahedron Lett, 2008, 49, 1111.
11. For related works on reductive coupling reactions of ynamides and aldehydes using stoichiometric amounts of Ti complex, see: (a) R. Tanaka, S. Hirano, H. Urabe, and F. Sato, Org. Lett., 2003, 5, 67;
12. (b) S. Hirano, R. Tanaka, H. Urabe, and F. Sato, Org. Lett., 2004, 6, 727;
13. (c) S. Hirano, Y. Fukudome, R. Tanaka, F. Sato, and H. Urabe, Tetrahedron, 2006, 62, 3896.
14. W. T. Wiesler and K. Nakanishi, J. Am. Chem. Soc, 1989, 111, 9205.
15. +] 354.2464, found 354.2458.
16. For nickel-catalyzed coupling of normal alkyne, aldehyde and silane via oxanickelacycle intermediate, see: (a) G. M. Mahandru, G. Liu, and J. Montgomery, J. Am. Chem. Soc., 2004, 126, 3698;
17. (b) K. Sa-ei and J. Montgomery, Org. Lett, 2006, 8, 4441;
18. (c) M. R. Chaulagain, G. J. Sormunen, and J. Montgomery, J. Am. Chem. Soc., 2007, 129, 9568;
19. 3B as a reducing reagent, see: (d) E. Oblinger and J. Montgomery, J. Am. Chem. Soc, 1997, 119, 9065;
20. (e) W.-S. Huang, J. Chan, and T. F. Jamison, Org. Lett., 2000, 2, 4221.
21. Recently, oxanickelacyclopentene from zero-valent nickel, aldehyde, and alkyne was isolated and its structure was elucidated by X-ray analysis. See: S. Ogoshi, T. Arai, M. Ohashi, and H. Kurosawa, Chem. Comunn., 2008, 1347.
22. P. R. McCarren, P. Liu, P. H.-Y. Cheong, T. F. Jamison, and K. N. Houk, J. Am. Chem. Soc., 2009, 131, 6654.