New efficient conditions for the reduction with NADH models

Synlett

Volumn , Issue 10, 1998, Pages 1144-1146

  Vasse, J L ^a   Charpentier, P ^a   Levacher, V ^a   Dupas, G ^a   Queguiner G ^a   Bourguignon, J ^a  

^a IRCOF   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001657039     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1876     Document Type: Article

References (22)

1. For reviews see a) Stout, D. M.; Meyers, A. I. Chem. Rev., 1982, 82, 223.
2. b) Ohno, A.; Ushida, S. in Lecture notes in Bio-Organic Chemistry. Mechanistic Models of Asymmetric Reductions; Springer-Verlag: Berlin, Heidelberg, New York, Tokyo, 1986; p1-105.
3. c) Inouye, Y.; Oda, J.; Baba, N. in Asymmetric Synthesis: Reductions with Chiral Dihydropyridine Reagents; Morrisson, J. D., Ed.; Academic Press: New York, London, 1983, 2; p92-124.
4. d) Burgess, V.A. ; Davies, S.G. and Skerly, R.T. Tetrahedron: Asymmetry, 1991, 2, 299.
5. a) Ohno, A.; Kimura, T.; Yamamoto, H.; Kim, S.G.; Oka, S.; Ohnishi, Y. Bull. Chem. Soc. Japan, 1977, 50, 1535.
6. b) Ohno, A.; Yamamoto, H.; Okamoto, T.; Oka, S.; Yamamoto, H. ; Okamoto, T. ; Oka, S.; Ohnishi, Y. Bull. Chem. Soc. Japan, 1977, 50, 2385.
7. c) Hughes, M.; Prince, R.H. J. Inorg. Nucl. Chem., 1978, 40, 703.
8. See for example The Sigma-Aldrich Library of Chemical Safety Data, 2nd edition; Lenga, R. E., Ed; 1988 ; p2180.
9. Cazin, J.; Trefouel, G.; Dupas, G.; Bourguignon, J.; Quéguiner, G. Tetrahedron, 1988, 44, 1079.
10. -
11. a) Levacher, V.; Boussad, N.; Dupas, G.; Bourguignon, J.; Quéguiner, G. Tetrahedron, 1992, 48, 831.
12. b) Berkous, R.; Dupas, G.; Bourguignon, J.; Quéguiner, G. Bull. Soc. Chim. Fr., 1994, 632.
13. a) Barett, A. G. M.: Nitroalkanes and Nitroalkenes in Synthesis. Tetrahedron Symposia-in-print, Tetrahedron, 1990, 46, 7313.
14. b) Perekalin, V. V. in Conjugated Nitro Compounds; Lipina, E. S.; Berestovitskay, V. M.; Efremov, D.A.; Eds; J. Wiley and Sons; 1994.
15. 1H NMR analysis.
16. Kabalma, G. W.; Gundi, L. H. M.; Warma, R. S. Tetrahedron, 1990, 46, 7443.
17. a) Creighton, D. J.; Hadju, J.; Sigman, D. S. J. Am. Chem. Soc., 1976, 98, 4619.
18. b) Shirai, M.; Chishina, T.; Tanaka, M. Bull. Chem. Soc. Japan., 1975, 48, 1079.
19. Levacher, V.; Valque, C.; Coupa, S.; Dupas, G.; Quéguiner, G.; Bourguignon, J. J. Heterocyclic Chem., 1996, 33, 1211. The e.e. was determined by HPLC on CHIRALCEL OD 10 μ, 250x4.6 mm, flow rate 1 mL/min, hexane/2-propanol 90/10. The temperature was 22 °C at 65 psi and the retention times were 10.82 (minor enantiomer) and 17.35 min (major enantiomer). Absolute configurations were not assigned.
20. Corey, E. J., Helal, C. J., Tetrahedron Lett., 1996, 37, 5675.
21. The e.e. in the reduction of 2-benzoylpyridine was determined by HPLC on CHIRALCEL OD 10 μ, 250x4.6 mm, flow rate 1 mL/ min, hexane/2-propanol 95/5. The temperature was 19 °C at 65 psi and the retention times were 15.18 (minor enantiomer) and 16.28 min (major enantiomer). Absolute configurations were not assigned.
22. Dupas, G.; Levacher, V.; Bourguignon, J.; Quéguiner, G., Heterocycles, 1994, 39, 405.