Asymmetric hydrogenation of N-substituted maleimides by cultured plant cells

Tetrahedron Asymmetry

Volumn 15, Issue 1, 2004, Pages 15-16

  Hirata, Toshifumi ^a   Takarada, Asuka ^a   Matsushima, Akihito ^a   Kondo, Yoko ^b   Hamada, Hiroki ^b  

^a HIROSHIMA UNIVERSITY   (Japan)

^b OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

MALEIMIDE DERIVATIVE; N PHENYL 2 METHYLMALEIMIDE; N PHENYL 2 METHYLSUCCINIMIDE; SUCCINIMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL BOND; ENANTIOSELECTIVITY; HYDROGENATION; NONHUMAN; PLANT CELL; PRIORITY JOURNAL; SUBSTITUTION REACTION; SUSPENSION CELL CULTURE; TOBACCO;

EID: 0348048817     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.10.033     Document Type: Article

References (22)

1. (a) For example: Matsumoto K., Tsutsumi S., Ihori T., Ohta H. J. Am. Chem. Soc. 112:1990;9614
2. (b) Fujii I., Lerner R.A., Janda K.D. J. Am. Chem. Soc. 113:1991;8528
3. (c) Henin F., Muzart J. Tetrahedron: Asymmetry. 9:1992;1161
4. (d) Yasukata T., Koga K. Tetrahedron: Asymmetry. 4:1993;35
5. (e) Fuji K., Tanaka K., Miyamoto H. Tetrahedron: Asymmetry. 4:1993;247
6. (f) Cavelier F., Gomez S., Jacquier R., Verducci J. Tetrahedron: Asymmetry. 4:1993;2501
7. (g) Ishihara K., Kaneeda M., Yamamoto H. J. Am. Chem. Soc. 116:1994;11179
8. (h) Cavelier F., Gomez S., Jacquier R., Verducci J. Tetrahedron Lett. 35:1994;2891
9. (i) Fuji K., Kawabata T., Kuroda A. J. Org. Chem. 60:1995;1914
10. (j) Piva O. J. Org. Chem. 60:1995;7879
11. (k) Takahashi T., Nakao N., Koizumi T. Chem. Lett. 1996;207
12. (l) Kataoka M., Kotaka A., Hasegawa A., Wada M., Yoshizumi A., Nakamori S., Shimizu S. Biosci. Biotechnol. Biochem. 66:2002;2651.
13. (a) Hirata T., Shimoda S., Gondai T. Chem. Lett. 2000;850
14. (b) Shimoda K., Izumi S., Hirata T. Bull. Chem. Soc. Jpn. 75:2002;813.
15. 7 supplemented with 3% sucrose and 10 mM 2,4-D under illumination (4000 lux). Each suspension cell was cultivated on a rotary shaker (75 rpm) at 25 °C for 3 weeks prior to use for biotransformation experiments.
16. Hirata T., Aoki T., Hirano Y., Ito T., Suga T. Bull. Chem. Soc. Jpn. 54:1981;3527.
17. Murashige T., Skoog F. Physiol. Plant. 15:1962;473.
18. Hamada H., Fuchikami Y., Ikematsu Y., Hirata T., Williams H., Scott A.I. Phytochemistry. 37:1994;1037.
19. Schenk R.U., Hildebrand A.C. Can. J. Botany. 50:1972;199.
20. 2), 126.4 (o-C in Ph), 128.6 (p-C in Ph), 129.1 (m-C in Ph), 132.0 (N-C in Ph), 175.4 (C=O), 179.5 (C=O).
21. Balenovic K., Bregant N. J. Chem. Soc. 1965;5131.
22. 1H NMR of the product 8 under the same conditions showed the methyl proton signals at δ 2.64 (d, J=7.0 Hz; integral value=0.55) and 2.56 (d, J=7.0 Hz; integral value=100).