Highly enantioselective azadiene diels-alder reactions catalyzed by chiral N-heterocyclic carbenes

Journal of the American Chemical Society

Volumn 128, Issue 26, 2006, Pages 8418-8420

  He, Ming ^a   Struble, Justin R ^a   Bode, Jeffrey W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENOID; HETEROCYCLIC COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIELS ALDER REACTION; ENANTIOSELECTIVITY;

EID: 33745685959     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja062707c     Document Type: Article

References (37)

1. Zeitler, K. Angew. Chem., Int. Ed. 2005, 44, 7506-7510.
2. (a) Johnson, J. S. Angew. Chem., Int. Ed. 2004, 43, 1326-1328.
3. (b) Christmann, M. Angew. Chem., Int. Ed. 2005, 44, 2632-2634.
4. (c) Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534-541.
5. Enders, D.; Kallfass, U. Angew. Chem., Int. Ed. 2002, 41, 1743-1745.
6. (a) Takikawa, H.; Hachisu, Y.; Bode, J. W.; Suzuki, K. Agnew. Chem., Int. Ed. 2006, 45, 3492-3494.
7. (b) Enders, D.; Niemeier, O.; Balensiefer, T. Angew. Chem., Int. Ed. 2006, 45, 1463-1467.
8. (a) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299.
9. (b) Kerr, M. S.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 8876-8877.
10. (c) Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2005, 127, 6284-6289.
11. (d) Enders, D.; Breuer, K.; Runsink, J.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1899-1902.
12. Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719-3726.
13. (a) Chow, K. Y.-C.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 8126-8127.
14. (b) Sohn, S. S.; Bode, J. W. Org. Lett. 2005, 7, 3873-3876.
15. (a) Reynolds, N. T.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 9518-9519.
16. (b) Chan, A.; Scheidt, K. A. Org. Lett. 2005, 7, 905-908.
17. (c) Zeitler, K. Org. Lett. 2006, 8, 637-640.
18. (a) Sohn, S. S.; Rosen, E. L.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370-14371.
19. (b) Burstein, C.; Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 6205-6208.
20. (c) He, M.; Bode, J. W. Org. Lett. 2005, 7, 3131-3134.
21. For a related strategy by nucleophilic additions to ketenes, see; (a) Hodous, B. L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 1578-1579.
22. (b) Wilson, J. E.; Fu, G. C. Angew. Chem., Int. Ed. 2004, 43, 6358-6360.
23. (a) Rovis has documented the NHC-catalyzed generation and enantioselective protonation of enolates from α,α′- dichloroaldehydes: Reynold, N.T.; Rovis, T. J. Am. Chem. Soc. 2005, 127, 16406-16407.
24. (b) For the diastereoselective protonation of enolates generated from α,β-epoxyaldehydes, see ref 7a.
25. For a reviews, see: (a) Boger, D. L. Tetrahedron 1983, 39, 2869-2939.
26. (b) Behforouz, M.; Ahmadian, M. Tetrahedron 2000, 56, 5259-5288.
27. Lancaster Synthesis (Alfa Aesar) Cat. No. 18481 (25 g/$50.97).
28. Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Org. Chem. 2005, 70, 5725-5728.
29. Satoh, T.; Hanaki, N.; Kuramochi, Y.; Inoue, Y.; Hosoya, K.; Sakai, K. Tetrahedron 2002, 58, 2533-2549.
30. (a) Boger, D. L.; Kasper, A. M. J. Am. Chem. Soc. 1989, 111, 1517-1519.
31. (b) Boger, D. L.; Corbett, W. L.; Curran, T. T.; Kasper, A. M. J. Am. Chem. Soc. 1991, 113, 1713-1729.
32. (a) Teng, M.; Fowler, F. W. Tetrahedron Lett. 1989, 30, 2481-2484.
33. (b) Sisti, N. J.; Motorina, I. A.; Tran Huu Dau, M. E.; Riche, C. Fowler, F. W.; Grierson, D. S. J. Org. Chem. 1996, 61, 3715-3728.
34. Berry, C. R.; Hsung, R. P. Tetrahedron 2004, 60, 7629-7636.
35. When less electrophilic enals are employed, the NHC catalyst reacts preferentially with the electrophilic imine. Thus, at the current stage of development, cinnamaldehyde and related substrates give only imine decomposition products under these conditions.
36. Fischer, C; Smith, S. W.; Powell, D. A.; Fu, G. C. J. Am. Chem. Soc. 2006, 128, 1472-1473.
37. For a chiral peptide-derived triazolium catalyst for the intermolecular aldehyde-imine cross-couplings, see; Mennen, S. M.; Gipson, J. D.; Kim, Y. R.; Miller, S. J. J. Am. Chem. Soc. 2005, 127, 1654-1655.