Cinchona-derived ammonium salts-catalyzed aza Diels-Alder reaction of Danishefsky's diene with imines

Tetrahedron

Volumn 67, Issue 6, 2011, Pages 1166-1170

  Park, Yohan ^a   Park, Eunyoung ^a   Jung, Hyojun ^a   Lee, Yeon Ju ^b   Jew, Sang Sup ^a   Park, Hyeung Geun ^a  

^a Seoul National University   (South Korea)

^b Korea Research Institute of Ships and Ocean Engineering   (South Korea)

Author keywords

Aza Diels Alder reaction; Cinchona ammonium catalyst

Indexed keywords

ALKADIENE; AMMONIA; CINCHONA ALKALOID; IMINE; LEWIS ACID; N 2',3',4' TRIFLUOROBENZYL O BENZYLCINCHONIDIUM BROMIDE; PYRIDONE DERIVATIVE; QUATERNARY AMMONIUM DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CINCHONA; DIELS ALDER REACTION; NONHUMAN; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS;

ALNUS; CINCHONA;

EID: 78751584675     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.12.002     Document Type: Article

References (43)

1. For the multiple roles of Cinchona alkaloid and their derivatives in chemical reactions, see:
2. K. Kacprzak, and J. Gawronski Synthesis 2001 961
3. A.E. Taggi, A.M. Hafez, and T. Lectka Acc. Chem. Res. 36 2003 10
4. For recent reviews on phase-transfer catalysis, see:
5. K. Maruoka, and T. Ooi Chem. Rev. 103 2003 3013
6. M.J. O'Donnell Acc. Chem. Res. 37 2004 506
7. B. Lygo, and B.I. Andrews Acc. Chem. Res. 37 2004 518
8. T. Hashimoto, and K. Maruoka Chem. Rev. 107 2007 5656
9. S.-s. Jew, and H.-g. Park Chem. Commun. 2009 7090
10. For our recent reports on asymmetric phase-transfer catalysis with Cinchona derivatives, see:
11. S.-s. Jew, B.-S. Jeong, M.-S. Yoo, H. Huh, and H.-g. Park Chem. Commun. 2001 1244
12. H.-g. Park, B.-S. Jeong, M.-S. Yoo, M.-k. Park, H. Huh, and S.-s. Jew Tetrahedron Lett. 42 2001 4645
13. H.-g. Park, B.-S. Jeong, M.-S. Yoo, J.-H. Lee, M.-k. Park, Y.-J. Lee, M.-J. Kim, and S.-s. Jew Angew. Chem., Int. Ed. 41 2002 3036
14. S.-s. Jew, M.-S. Yoo, B.-S. Jeong, I.Y. Park, and H.-g. Park Org. Lett. 4 2002 4245
15. M.-S. Yoo, B.-S. Jeong, J.-H. Lee, H.-g. Park, and S.-s Jew Org. Lett. 7 2005 1129
16. S.-s. Jew, J.-H. Lee, B.-S. Jeong, M.-S. Yoo, M.-J. Kim, Y.-J. Lee, J. Lee, S.-h. Choi, K. Lee, M.S. Lah, H.-g. Park, Angew. Chem., Int. Ed. 44 2005 1383
17. W. Carruthers Cycloaddition Reactions in Organic Synthesis 1990 Pergamon Oxford
18. W. Oppolazer L.A. Paquette, Comprehensive Organic Synthesis Vol. 5 1991 Pergamon Oxford p 315
19. S.M. Weinreb Hetero dienophile additions to dienes B.M. Trost, I. Fleming, Comprehensive Organic Synthesis Vol. 5 1991 Pergamon Oxford p 401
20. H. Waldmann Synthesis 1994 535
21. For aza-Diels-Alder reactions with Danishefsky's diene:
22. J. Collin, N. Jaber, and M.I. Lannou Tetrahedron Lett. 42 2001 7405
23. H. Laurent-Robert, B. Garrigues, and J. Dubac Synlett 2000 1160
24. T. Ali, K.K. Chauhan, and C.G. Frost Tetrahedron Lett. 40 1999 5621
25. S. Kobayashi, H. Ishitani, and S. Nagayama Synthesis 1995 1195
26. S. Kobayashi, H. Ishitani, and S. Nagayama Chem. Lett. 1995 423
27. S. Kobayashi, K. Manabe, and Y. Mori Tetrahedron 57 2001 2537
28. Y. Yuan, X. Li, and K. Ding Org. Lett. 4 2002 3309
29. S. Kobayashi, C. Loncaric, and K. Manabe Chem. Commun. 5 2003 574
30. S. Kobayashi, C. Loncaric, and K. Manabe Adv. Synth. Catal. 345 2003 475
31. R. Wilhelm, and V. Jurčík Org. Biomol. Chem. 3 2005 239
32. E.J. Corey, F. Xu, and M.C. Noe J. Am. Chem. Soc. 119 1997 12414
33. S. Colonna, A. Re, G. Gelbard, and E. Cesarotti J. Chem. Soc. Perkin Trans. 1979 2248
34. T. Shioiri, A. Ando, T. Miura, and T. Tatematsu Tetrahedron Lett. 34 1993 1507
35. T. Ooi, M. Kameda, and K. Maruoka J. Am. Chem. Soc. 125 2003 5139
36. M.A. Mohamed, K.-i. Yamada, and K. Tomioka Tetrahedron Lett. 50 2009 3436
37. S. Cicchi, J. Revuelta, A. Zanobini, M. Betti, and A. Brandi Synlett 2003 2305
38. J. Revuelta, S. Cicchi, and A. Brandi J. Org. Chem. 70 2005 5636
39. K.C. Nicolaou, C.J.N. Mathison, and T. Montagnon Angew. Chem., Int. Ed. 42 2003 4077
40. K.C. Nicolaou, C.J.N. Mathison, and T. Montagnon J. Am. Chem. Soc. 126 2004 5192
41. M. Wolter, C. Borm, E. Merten, R. Wartchow, and E. Winterfeldt Eur. J. Org. Chem. 2001 4051
42. S.-M. Paek, N.-J. Kim, D. Shin, J.-K. Jung, J.-W. Jung, D.-J. Chang, H. Moon, and Y.-G. Suh Chem. - Eur. J. 16 2010 4623
43. T. Nemoto, E. Yamamoto, R. Franzén, T. Fukuyama, R. Wu, T. Fukamachi, H. Kobayashi, and Y. Hamada Org. Lett. 12 2010 872