Zinc-mediated Reductive Dimerization Cyclization of Ethyl Arylmethylidene cyanoacetates in Aqueous Media

(Note: The full text of this document is currently only available in the PDF Version )

Lei Wang and Yongmin Zhang


Abstract

Zinc-mediated reductive dimerization–cyclization of ethyl arylmethylidenecyanoacetates occurs to give diethyl 2-amino-3-cyano-4,5-diaryl-1,3-cyclopentenedicarboxylates in moderate to good yields the trans, trans-form isomer being the major product.


References

  1. (a) J. J. Bloomfield, D. C. Owsley and J. M. Nelka, Org. React., 1976, 23, 259 CAS; (b) R. Bartezko, R. Gleiter, J. L. Muthard and L. A. Paquette, J. Am. Chem. Soc., 1978, 100, 5589 CrossRef; (c) K. Ruhlman, Synthesis, 1971, 236 CrossRef; (d) A. Furstner, R. Csuk, C. Rohrer and H. Weidmann, J. Chem. Soc., Perkin Trans. 1, 1988, 1729 RSC.
  2. (a) J. Inanaga, Y. Handa, T. Tabuchi, K. Otsubo, M. Yamaguchi and T. Hanamoto, Tetrahedron Lett., 1991, 32, 6557 CrossRef CAS; (b) S. Kanemasa, H. Yamamoto and S. Kobayashi, Tetrahedron Lett., 1996, 37, 8505 CrossRef CAS; (c) L. Zhou and Y. Zhang, Tetrahedron Lett., 1997, 38, 8063 CrossRef CAS.
  3. (a) C. J. Li and T. H. Chan, Organic Reactions in Aqueous Media, Wiley, New York, 1997 Search PubMed; (b) T. H. Chan and M. B. Isaac, Pure & Appl. Chem., 1996, 68, 919 CrossRef CAS; (c) Y. Yamamoto and N. Asao, Chem. Rev., 1993, 93, 2207 CrossRef CAS; (d) C. J. Li, Chem. Rev., 1993, 93, 2023 CrossRef CAS; (e) A. Lubineau, J. Auge and Y. Queneau, Synthesis, 1994, 741 CrossRef CAS; (f) C. J. Li, Tetrahedron, 1996, 52, 5643 CrossRef CAS.
  4. M. Hulce and T. LaVaute, Tetrahedron Lett., 1988, 29, 525 CrossRef CAS.
  5. M. C. Barden and J. Schwartz, J. Am. Chem. Soc., 1996, 118, 5484 CrossRef CAS.
  6. C. J. Li, Y. Meng, X. H. Yi, J. Ma and T. H. Chan, J. Org. Chem., 1997, 62, 8632 CrossRef CAS.
  7. (a) C. Petrier and J. L. Luche, J. Org. Chem., 1985, 50, 910 CrossRef CAS; (b) S. R. Wilson and M. E. Guazzaroni, J. Org. Chem., 1989, 54, 3087 CrossRef CAS.
  8. (a) T. H. Chan, C. J. Li and Z. J. Wei, J. Chem. Soc., Chem. Commun., 1990, 505 RSC; (b) D. Marton, D. Stivanello and G. Tagliavini, J. Org. Chem., 1996, 61, 2731 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.