Organocatalysis using protonated 1,2-diamino-1,2-diphenylethane for asymmetric Diels-Alder reaction

Tetrahedron Letters

Volumn 46, Issue 36, 2005, Pages 5991-5994

  Kim, Kyoung Hoon ^a   Lee, Seil ^a   Lee, Dae Woong ^a   Ko, Dong Hyun ^a   Ha, Deok Chan ^a  

^a Korea University   (South Korea)

Author keywords

Aldehydes; Ammonium salts; Asymmetric Diels Alder; Cyclopentadiene; Organocatalysis

Indexed keywords

AMMONIUM DERIVATIVE; BENZENE DERIVATIVE; CROTONALDEHYDE; CYCLOPENTADIENE DERIVATIVE; DIAMINE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CYCLOADDITION; DIELS ALDER REACTION; ENANTIOSELECTIVITY; PROTON TRANSPORT;

BETULACEAE;

EID: 23344442773     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.07.025     Document Type: Article

References (34)

1. R. Noyori Asymmetric Catalysis in Organic Synthesis 1994 John Wiley and Sons New York
2. E.N. Jacobsen A. Pfaltz H. Yamamoto Comprehensive Asymmetric Catalysis 1999 Springer Berlin
3. I. Ojima Catalytic Asymmetric Synthesis 2000 Wiley-VCH New York
4. M. Beller C. Bolm Transition Metals for Organic Synthesis 2004 Wiley-VCH Weinheim
5. For reviews on organocatalysis, see: E.R. Jarvo, and S.J. Miller Tetrahedron 58 2002 2481
6. B. List Tetrahedron 58 2002 5573
7. P.I. Dalko, and L. Moisan Angew. Chem., Int. Ed. 43 2004 5138
8. Acc. Chem. Res. 37 8 2004 (a special issue on organocatalysis)
9. C. Bolm, T. Rantanen, I. Schiffers, and L. Zani Angew. Chem., Int. Ed. 44 2005 1758
10. For reviews on enantioselective Diels-Alder reactions, see: W. Oppolzer Angew. Chem., Int. Ed. Engl. 23 1984 876
11. H. Kagan, and O. Riant Chem. Rev. 92 1992 1007
12. E.J. Corey Angew. Chem., Int. Ed. 41 2002 1650
13. K. Ishihara, and H. Yamamoto J. Am. Chem. Soc. 116 1994 1561
14. K. Ishihara, H. Kurihara, and H. Yamamoto J. Am. Chem. Soc. 118 1996 3049
15. K. Ishihara, H. Kurihara, M. Matsumoto, and H. Yamamoto J. Am. Chem. Soc. 120 1998 6920
16. E.J. Corey, T. Shibata, and T.W. Lee J. Am. Chem. Soc. 124 2002 3808
17. D.H. Ryu, T.W. Lee, and E.J. Corey J. Am. Chem. Soc. 124 2002 9992
18. D.H. Ryu, and E.J. Corey J. Am. Chem. Soc. 125 2003 6388
19. D.H. Ryu, G. Zhou, and E.J. Corey J. Am. Chem. Soc. 126 2004 4800
20. T. Schuster, M. Bauch, G. Durner, and M.W. Gobel Org. Lett. 2 2000 179
21. Y. Huang, A.K. Unni, A.N. Thadani, and V.H. Rawal Nature 424 2003 146
22. A.N. Thadani, A.R. Stankovic, and V.H. Rawal Proc. Natl. Acad. Sci. U.S.A. 101 2004 5846
23. A.K. Unni, N. Takenaka, H. Yamamoto, and V.H. Rawal J. Am. Chem. Soc. 127 2005 1336
24. K.A. Ahrendt, C.J. Borths, and D.W.C. MacMillan J. Am. Chem. Soc. 122 2000 4243
25. W.S. Jen, J.J.M. Wiener, and D.W.C. MacMillan J. Am. Chem. Soc. 122 2000 9874
26. A.B. Northrup, and D.W.C. MacMillan J. Am. Chem. Soc. 124 2002 2458
27. D.H. Aue, H.M. Webb, and M.T. Bowers J. Am. Chem. Soc. 95 1973 2699
28. R. Yamdagni, and P. Kebarle J. Am. Chem. Soc. 95 1973 3504
29. K. Manabe, Y. Mori, and S. Kobayashi Tetrahedron 57 2001 2537
30. F. Fringuelli, O. Piermatti, F. Pizzo, and L. Vaccaro Eur. J. Org. Chem. 2001 439
31. 4), concentrated in vacuo, and the residue was purified by silica gel chromatography to give 6c in 72% overall yield.
32. R = 42.90 min.
33. S.-i. Hashimoto, N. Komeshima, and K. Koga J. C. S. Chem. Commun. 1979 437
34. H. Takemura, N. Komeshima, I. Takahashi, S.-i. Hashimoto, N. Ikota, K. Tomioka, and K. Koga Tetrahedron Lett. 28 1987 5687