Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Enantioselective Hydrogenation of (E)-and (Z)-Isomeric Ethyl 3-Acetamidobutenoates with Rh-Bisphosphine Complexes: Effects of Substrate Geometry and Solvents on Reaction Rates and Catalyst Reusability

  • Zhang, Yong Jian (School of Chemistry and Chemical Technology, Shanghai Jiao Tong University) ;
  • Rho, Eun-Joo (Life Sciences Division, Korea Institute of Science and Technology) ;
  • Lee, Sang-Gi (Life Sciences Division, Korea Institute of Science and Technology)
  • Published : 2005.08.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Enantioselective Synthesis of Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997
  2. Cole, D. C. Tetrahedron 1994, 50, 9517 https://doi.org/10.1016/S0040-4020(01)85527-7
  3. Gellman, S. H. Acc. Chem. Res. 1998, 31, 173 https://doi.org/10.1021/ar960298r
  4. Tang, T.; Ellman, J. A. J. Org. Chem. 1999, 64, 12 https://doi.org/10.1021/jo9820824
  5. Sibi, M. P.; Shay, H. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615 https://doi.org/10.1021/ja980520i
  6. Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431 https://doi.org/10.1021/ja973527t
  7. Chung, X. X. Tetrahedron: Asymmetry 1997, 8, 5 https://doi.org/10.1016/S0957-4166(96)00496-X
  8. Dumas, F.; Mezrhab, B.; d'Angelo, J. J. Org. Chem. 1996, 61, 2293 https://doi.org/10.1021/jo951414r
  9. Davis, F. A.; Szewczyk, J. M.; Reddy, R. E. J. Org. Chem. 1996, 61, 2222 https://doi.org/10.1021/jo951917x
  10. Enders, D.; Wahl, H.; Bettray, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 455 https://doi.org/10.1002/anie.199504551
  11. Achiwa, K.; Soga, T. Tetrahedron Lett. 1978, 13, 1119
  12. Furukawa, M.; Okawara, T.; Noguchi, Y.; Terawaki, Y. Chem. Pharm. Bull. 1979, 27, 2223 https://doi.org/10.1248/cpb.27.2223
  13. Zhu, G.; Chen, Z.; Zhang, X. J. Org. Chem. 1999, 64, 6907 https://doi.org/10.1021/jo990565h
  14. Heller, D.; Holz, J.; Drexler, H.-J.; Lang, J.; Drauz, K.; Krimmer, H.-p.; Börner, A. J. Org. Chem. 2001, 66, 6816 https://doi.org/10.1021/jo010445l
  15. Yasutake, M.; Gridnev, I. D.; Higashi, N.; Imamoto, T. Org. Lett. 2001, 3, 1701 https://doi.org/10.1021/ol0158967
  16. Lubell, W. D.; Kitamura, M.; Noyori, R. Tetrahedron: Asymmetry 1991, 2, 543 https://doi.org/10.1016/S0957-4166(00)86107-8
  17. Pena, D.; Minnaard, A. J.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 14552 https://doi.org/10.1021/ja028235t
  18. Tang, W.; Zhang, X. Org. Lett. 2002, 4, 4159 https://doi.org/10.1021/ol026935x
  19. Holz, J.; Monsees, A.; Jiao, H.; You, J.; Komarov, I. V.; Fischer, C.; Drauz, K.; Borner, A. J. Org. Chem. 2003, 68, 1701 https://doi.org/10.1021/jo020453h
  20. Lee, S.-g.; Zhang, Y. J.; Song, C. E.; Lee, J. K.; Choi, J. H. Angew. Chem. Int. Ed. 2002, 41, 847 https://doi.org/10.1002/1521-3773(20020301)41:5<847::AID-ANIE847>3.0.CO;2-F
  21. Zhang, Y. J.; Lee, S.-g. Org. Lett. 2002, 4, 2429 https://doi.org/10.1021/ol0261884
  22. Lee, S.-g.; Zhang, Y. J.; Piao, J. Y.; Yoon, H.; Song, C. E.; Choi, J. H.; Hong, J. Chem. Commun. 2003, 2624
  23. Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667 https://doi.org/10.1021/cr010338r
  24. Baudequin, C.; Baudoux, J.; Levillain, J.; Cahard, D.; Gaumont, A.-C.; Plaquevent, J.-C. Tetrahedron: Asymmetry 2003, 14, 3081 https://doi.org/10.1016/S0957-4166(03)00596-2
  25. Song, C. E. Chem. Comm. 2004, 1033
  26. Lee, S.-g.; Park, J. H. Bull. Korean Chem. Soc. 2002, 23, 1367 https://doi.org/10.5012/bkcs.2002.23.10.1367
  27. Heller, D.; Drexler, H.-J.; You, J.; Baumann, W.; Drauz, K.; Krimmer, H.-P.; Börner, A. Chem. Eur. J. 2002, 8, 5196 https://doi.org/10.1002/1521-3765(20021115)8:22<5196::AID-CHEM5196>3.0.CO;2-P
  28. Jerphagnon, T.; Renaud, J.-L.; Demonchaux, P.; Ferreira, A.; Bruneau, C. Tetrahedron:Asymmetry 2003, 14, 1973 https://doi.org/10.1016/S0957-4166(03)00359-8

Cited by

  1. The first chemoselective tandem acylation of the Blaise reaction intermediate: a novel method for the synthesis of α-acyl-β-enamino esters, key intermediate for pyrazoles pp.41, 2008, https://doi.org/10.1039/b813369g
  2. Enantioselective Hydrogenation of (E)- and (Z)-Isomeric Ethyl 3-Acetamidobutenoates with Rh-Bisphosphine Complexes: Effects of Substrate Geometry and Solvents on Reaction Rates and Catalyst Reusabilit vol.37, pp.1, 2006, https://doi.org/10.1002/chin.200601032
  3. Synthesis of β-aminoacid derivatives via enantioselective hydrogenation of β-substituted-β-(acylamino)acrylates vol.252, pp.5, 2005, https://doi.org/10.1016/j.ccr.2007.09.013