Preparation of axially chiral quinolinium salts related to NAD + models: New investigations of these biomimetic models as 'chiral amide-transferring agents'

Tetrahedron Asymmetry

Volumn 15, Issue 24, 2004, Pages 3919-3928

  Leleu, Stéphane ^a   Papamicaël, Cyril ^a   Marsais, Francis ^a   Dupas, Georges ^a   Levacher, Vincent ^a  

^a Normandie Université   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLAMINE; NICKEL; NICOTINAMIDE ADENINE DINUCLEOTIDE; PIPERIDINE; QUINOLINE DERIVATIVE;

ARTICLE; BIOMIMETICS; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHIRALITY; PRIORITY JOURNAL; QUANTUM YIELD; STEREOCHEMISTRY;

EID: 9944263398     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.11.004     Document Type: Article

References (50)

1. Y. Inouye, J. Oda, and N. Baba Reductions with Chiral Dihydropyridine Reagents J.D. Morrison Asymmetric Synthesis Vol. 2 1983 Academic New York, London 92
2. A. Ohno, and S. Ushida Mechanistic Models of Asymmetric Reductions E. Baulieu L. Jaenicke V. Massey R.J.P. Williams E.L. Winnacker B. Zerner Lecture Notes in Bio-Organic Chemistry 1986 Springer Berlin 1
3. V.A. Burgess, S.G. Davies, and R.T. Skerj Tetrahedron: Asymmetry 2 1991 299
4. G. Dupas, V. Levacher, J. Bourguignon, and G. Quéguiner Heterocycles 39 1994 405
5. V. Levacher, G. Dupas, G. Quéguiner, and J. Bourguignon Trends Heterocycl. Chem. 4 1995 293
6. K. Ichinose, M. Kodera, J. Leeper, and R. Battersby J. Chem. Soc., Perkin Trans. 1 1999 879
7. W.K. Fife Heterocycles 22 1984 2375
8. A. Goto, and H. Kishimoto J. Chem. Soc., Perkin Trans. 2 1990 73
9. R.E. Lyle, and G.J. Gauthier Tetrahedron Lett. 1965 4615
10. A. Clerici, and O. Porta Tetrahedron Lett. 1980 1675
11. R.N. Lindquist, and E.H. Cordes J. Am. Chem. Soc. 1968 1269
12. J.F.J. Engbersen, A. Koudijs, H.M. Sleiderink, and M.C.R. Franssen J. Chem. Soc., Perkin Trans. 2 1990 79
13. W.K. Fife J. Org. Chem. 48 1983 1375
14. R. Foster, and C.A. Fyfe Tetrahedron 25 1969 1489
15. A.G. Anderson, and G. Berkelhammer J. Org. Chem. 1958 1109
16. S.W. Damji, and C.A. Fyfe J. Org. Chem. 44 1979 1757
17. O. Piepers, and R.M. Kellogg J. Chem. Soc., Chem. Commun. 1980 1147
18. S.W.H. Damji, and C.A. Fyfe J. Org. Chem. 44 1979 1761
19. J.C. Speelman, and R.M. Kellogg J. Org. Chem. 55 1990 647
20. W.H. Gündel Liebigs Ann. Chem. 1980 1350
21. J.W. Bunting, and J. Bolton Tetrahedron 42 1986 1007
22. F.M. Moracci, B.D. Rienzo, S. Tortorella, and F. Liberatore Tetrahedron 36 1980 785
23. S.A.G.F. Angelino, A. Van Veldhuizen, D.J. Buurman, and H.C. Van Der Plas Tetrahedron 40 1984 433
24. E. Okada, T. Sakaemura, and N. Shimomura Chem. Lett. 2000 50
25. J.A. Zoltewicz, L.S. Helmick, and J.K. O'Halloran J. Org. Chem. 41 1976 1303
26. H.C. Van Der Plas, and D.J. Buurman Tetrahedron Lett. 25 1984 3763
27. S.A.G.F. Angelino, B.H. Van Valkengoed, D.J. Buurman, H.C. Van Der Plas, and F. Müller J. Heterocycl. Chem. 21 1984 107
28. S.H. Mashraqui, and R.M. Kellogg J. Am. Chem. Soc. 105 1983 7792
29. R.M. Kellogg Angew. Chem., Int. Ed. Engl. 96 1984 769
30. J.-L. Vasse, V. Levacher, J. Bourguignon, and G. Dupas Chem. Commun. 2002 2256
31. J.-L. Vasse, G. Dupas, J. Duflos, G. Quéguiner, J. Bourguignon, and V. Levacher Tetrahedron Lett. 42 2001 3713
32. J.-L. Vasse, G. Dupas, J. Duflos, G. Quéguiner, J. Bourguignon, and V. Levacher Tetrahedron Lett. 42 2001 4613
33. C.C. Cheng, and S.J. Yan The Friedlander synthesis of quinolines Org. React. 28 1982 37
34. W. Borsche, and W. Ried Liebigs Ann. Chem. 554 1943 269
35. W. Borsche, and J. Barthenheier Liebigs Ann. Chem. 548 1941 50
36. F. Marsais, A. Godard, and G. Quéguiner J. Heterocycl. Chem. 26 1989 1589
37. N.S. Narasimhan, and R.S. Mali Synthesis 1983 957
38. G. Hilmersson, and O. Davidsson Organometallics 14 1995 912
39. M. Iyoda, H. Otsuka, K. Sato, N. Nisato, and M. Oda Bull. Chem. Soc. Jpn. 63 1990 80
40. I. Colon, and D.R. Kelsey J. Org. Chem. 51 1986 2627
41. A. Ohno, A. Tsutsumi, N. Yamazaki, M. Okamura, Y. Mikata, and M. Fujii Bull. Chem. Soc. Jpn. 69 1996 1679
42. M.F. Semmelhack, P. Helquist, L.D. Jones, L. Keller, L. Mendelson, L.S. Ryono, J. Gorzynski Smith, and R.D. Stauffer J. Am. Chem. Soc. 103 1981 6460
43. S. Thayumanavan, P. Beak, and D.P. Curran Tetrahedron Lett. 37 1996 2899
44. J. Clayden, and L.W. Lai Tetrahedron Lett. 37 1996 3163
45. J. Clayden, P. Johnson, J.H. Pink, and M. Helliwell J. Org. Chem. 65 2000 7033
46. J. Clayden Chem. Commun. 2004 127
47. This atropenantioselective approach would lead to the first enantioselective preparation of the atropisomeric amide 20, a precursor of a highly performant chiral NADH model: Y. Mikata, K. Hayashi, K. Mizukami, S. Matsumoto, S. Yano, N. Yamazaki, and A. Ohno Tetrahedron Lett. 41 2000 1035
48. V.G.S. Box, N. Marinovic, and G.P. Yiannikouros Heterocycles 32 1991 245
49. A. Ohno, M. Kashiwagi, Y. Ishihara, S. Ushida, and S. Oka Tetrahedron 42 1986 961
50. P. Li, and J.-C. Xu Tetrahedron 56 2000 8119