Enantioselective reduction of oxime ethers with borane catalyzed by polymer-supported 2-piperazinemethanol

Journal of Organic Chemistry

Volumn 65, Issue 18, 2000, Pages 5879-5881

  Itsuno, Shinichi ^a   Matsumoto, Takeshi ^a   Sato, Daisuke ^b   Inoue, Tsutomu ^b  

^a TOYOHASHI UNIVERSITY OF TECHNOLOGY   (Japan)

^b NIPPON SODA CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

OXIME DERIVATIVE; POLYMER;

CHEMICAL REACTION; CHIRALITY; CROSS LINKING; ENANTIOMER; NOTE; REDUCTION;

EID: 0033828494     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0007837     Document Type: Note

References (20)

1. Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895.
2. Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
3. Inoue, T.; Sato, D.; Komura, K.; Itsuno, S. Tetrahedron Lett. 1999, 40, 5379.
4. Reviews of polymer-supported chiral catalysts: (a) Itsuno, S. In Polymeric Materials Encyclopedia; Synthesis, Properties and Applications; Salamone, J. C., Ed.; CRC: Boca Raton, FL, 1996; Vol. 10, p 8078.
5. (b) Blossey, E. C.; Ford, W. T. In Comprehensive Polymer Science. The Synthesis, Characterization, Reactions and Applications of Polymers; Allen, G., Bevington, J. C., Eds.; Pergamon: New York, 1989; Vol. 6, p 81.
6. (c) Pu, L. Chem. Eur. J. 1999, 5, 2227.
7. Itsuno, S. In Handbook on Lewis Acid - Application in Organic Synthesis; Yamamoto, H., Ed.; Wiley-VCH: in press.
8. (a) Itsuno, S. Org. React. 1998, 52, 395.
9. (b) Itsuno, S. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 1, Chapter 1, p 289.
10. (c) Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1987.
11. For other examples of supported chiral oxazaborolidines, see: (a) Itsuno, S.; Nakano, M.; Ito, K.; Hirao, A.; Owa, M.; Kanda, N.; Nakahama, S. J. Chem. Soc., Perkin Trans. 1 1985, 2615.
12. (b) Caze, C.; El Moualij, N.; Hodge, P.; Lock, C. J.; Ma, J. J. Chem. Soc., Perkin Trans. 1 1995, 345.
13. (c) Franot, C.; Stone, G. B.; Engeli, P.; Spöndlin, C.; Waldvogel, E. Tetrahedron: Asymmetry 1995, 6, 2755.
14. (d) Felder, M.; Giffels, G.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1975.
15. (e) Giffels, G.; Beliczey, J.; Felder, M.; Kragl, U. Tetrahedron: Asymmetry 1998, 9, 691.
16. Masui, M.; Shioiri, T. Tetrahedron Lett. 1998, 39, 5199.
17. Ishizone, T.; Tsuchiya, J.; Hirao, A.; Nakahama, S. Macromolecules 1992, 25, 4840.
18. Theilaker, W.; Winkler, H. G. Chem. Ber. 1954, 87, 691.
19. Warren, M. E.; Smith, H. E. J. Am. Chem. Soc. 1965, 87, 1757.
20. Yamamoto, Y.; Shimoda, H.; Oda, J.; Inoue, Y. Bull. Chem. Soc. Jpn. 1976, 49, 3247.