Cyclization reaction of cyano-substituted unsaturated esters prompted by conjugate addition of organoborons

Organic Letters

Volumn 9, Issue 5, 2007, Pages 741-743

  Miura, Tomoya ^a   Harumashi, Tatsuro ^a   Murakami, Masahiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33947156298     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062882y     Document Type: Article

References (24)

1. Reviews: (a) Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365.
2. (b) Grigg, R.; Sridharan, V. J. Organomet. Chem. 1999, 576, 65.
3. (c) Miura, T.; Murakami, M. Chem. Commun. 2007, 217.
4. Agapiou, K.; Cauble, D. F.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4528.
5. For the addition of Zn enolates to nitliles, see: Blaise, E. E. C. R. Hebd. Seances Acad. Sci. 1901, 132, 478.
6. (a) Miura, T.; Nakazawa, H.; Murakami, M. Chem. Commun. 2005, 2855.
7. (b) Miura, T.; Murakami, M. Org. Lett. 2005, 7, 3339.
8. (a) Ueura, K.; Satoh, T.; Miura, M. Org. Lett. 2005, 7, 2229.
9. (b) Ueura, K.; Miyamura, S.; Satoh, T.; Miura, M. J. Organomet. Chem. 2006, 691, 2821.
10. For Rh-catalyzed conjugate addition/electrophilic trapping reaction, see: (a) Matsuda, I.; Takahashi, K.; Sato, S. Tetrahedron Lett. 1990, 31, 5331.
11. (b) Taylor, S. J.; Duffey, M. O.; Morken, J. P. J. Am. Chem. Soc. 2000, 122, 4528.
12. (c) Yoshida, K.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 10984.
13. (d) Cauble, D. F.; Gipson, J. D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110.
14. (e) Bocknack, B. M.; Wang, L.-C.; Krische, M. J. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5421.
15. (f) Nicolaou, K. C.; Tang, W.; Dagneau, P.; Faraoni, R. Angew. Chem., Int. Ed. 2005, 44, 3874.
16. Fustero, S.; García de la Torre, M.; Jofré, V.; Carlón, R. P.; Navarro, A.; Fuentes, A. S.; Carrió, J. S. J. Org. Chem. 1998, 63, 8825.
17. Kramer, G. W.; Brown, H. C. J. Organomet. Chem. 1974, 73, 1.
18. Another reaction pathway involving transmetalation of A with 2a to generate a boron enolate cannot be excluded, as suggested by one of the reviewers, to whom the authors are grateful.
19. 4. The solvent was removed under reduced pressure, and the residue was purified by preparative thin-layer chromatography (dichloromethane) to give the product 3. The second chromatography (hexane/ethyl acetate) was carried out in some cases to remove small amounts of impurities.
20. For a review on catalytic asymmetric cascade transformations triggered by conjugate additions, see: Guo, H.-C.; Ma, J.-A. Angew. Chem., Int. Ed. 2006, 45, 354.
21. For a review on Rh-catalyzed asymmetric conjugate addition, see: Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
22. Zhang, X.; Mashima, K.; Koyano, K.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Takaya, H. Tetrahedron Lett. 1991, 32, 7283.
23. Fustero, S.; Piera, J.; Sanz-Cervera, J. F.; Catalán, S.; Ramírez de Arellano, C. Org. Lett. 2004, 6, 1417.
24. Di Raddo, P.; Harvey, R. G. Tetrahedron Lett. 1988, 29, 3885.