Enecarbamates as imine surrogates: Nucleophilic addition of 1,3-dicarbonyl compounds to enecarbamates

Organic Letters

Volumn 8, Issue 21, 2006, Pages 4923-4925

  Kobayashi, Shu ^a   Gustafsson, Tomas ^a   Shimizu, Yusuke ^a   Kiyohara, Hiroshi ^a   Matsubara, Ryosuke ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33750366006     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0620186     Document Type: Article

References (22)

1. (a) Kibayashi, C. Chem. Pharm. Bull. 2005, 53, 1375.
2. (b) Joullié, M. M.; Richard, D. J. Chem. Commun. 2004, 2011.
3. Reviews: (a) Denmark, S. E.; Nicaise, O. J.-C. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Heidelberg, 1999; pp 923-961.
4. (b) Kleinmann, E. F. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 2, Chapter 4.1.
5. (c) Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. 1998, 37, 1044.
6. (d) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
7. To overcome this problem, a synthetic equivalent has been used. For an example, see: (a) Côté, A.; Boezio, A. A.; Charette, A. B. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5405.
8. (b) Pearson, W. H.; Lindbeck, A. C.; Kampf, J. W. J. Am. Chem. Soc. 1993, 115, 2622.
9. (c) Ha, H.-J.; Ahn, Y.-G. Synth. Commun. 1995, 25, 969.
10. (d) Katritzky, A. R.; Rachwal, S.; Hitchings, G. J. Tetrahedron 1991, 47, 2683.
11. Gridnev, I. D.; Imamoto, T. Acc. Chem. Res. 2004, 37, 633 and references therein.
12. (a) Matsubara, R.; Nakamura, Y.; Kobayashi, S. Angew. Chem., Int. Ed. 2004, 43, 1679.
13. (b) Matsubara, R.; Nakamura, Y.; Kobayashi, S. Angew. Chem. Int. Ed. 2004, 43, 3258.
14. (c) Matsubara, R.; Vital, P.; Nakamura, Y.; Kiyohara, H.; Kobayashi, S. Tetrahedron 2004, 60, 9769.
15. (d) Fossey, J. S.; Matsubara, R.; Vital, P.; Kobayashi, S. Org. Biomol. Chem. 2005, 3, 2910.
16. (e) Matsubara, R.; Kawai, N.; Kobayashi, S. Angew. Chem., Int. Ed. 2006, 45, 3814.
17. 2 and diphenylethylenediamine ligand was employed.
18. A similar reaction mechanism was reported in palladium enolate chemistry. Sodeoka, M.; Hamashima, Y. Bull. Chem. Soc. Jpn. 2005, 78, 941 and references therein.
19. Mecozzi, T.; Petrini, M. Synlett 2000, 73 and references therein.
20. Recent examples of direct Mannich-type reactions using 1,3-dicarbonyl compounds. (a) Ting, A.; Lou, S.; Schaus, S. E. Org. Lett. 2006, 8, 2003.
21. (b) Tillman, A. L.; Ye, J. X.; Dixon, D. J. Chem. Commun. 2006, 1191.
22. (c) Terada, M.; Sorimachi, K.; Uraguchi, D. Synlett 2006, 133.