Stereoisomeric Styryl-substituted Pyrrolidines, 3,7-Diazobicyclo[3.3.0]octanes and 2-Styrylpyrroles from Cinnamaldehyde Iminium-N-methanide 1,3-Dipoles

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Richard N. Butler and Derval M. Farrell


Abstract

The reaction of cinnamaldehyde N-aryliminium methanide 1,3-dipoles with dimethyl maleate, dimethyl fumarate and some N-arylmaleimides gives equal mixtures of stereoisomeric substituted pyrrolidines and a route to 2-styrylpyrroles with dimethyl acetylenedicarboxylate.


References

  1. I. Coldham, A. J. Collis, R. J. Mould and D. E. Robinson, Synthesis, 1995, 1147 CrossRef CAS.
  2. For a review see, J. W. Lown, in 1,3-Dipolar Cycloaddition Chemistry, ed. A. Padwa, Wiley, New York, 1984, vol. 1, p. 653 Search PubMed.
  3. A. Padwa and L. Hamilton, Tetrahedron Lett., 1965, 4363 CrossRef CAS; C. Wittland, M. Arend and N. Risch, Synthesis, 1996, 367 CrossRef CAS.
  4. Y. Gelas-Mialhe, E. Tourad and R. Vessiere, Can. J. Chem., 1982, 60, 2830 CAS; R. Grigg, J. Montgomery and A. Somasunderam, Tetrahedron, 1992, 48, 10431 CrossRef CAS.
  5. O. Tsuge, S. Kanemasa, M. Ohe, K. Yorozu, S. Takenaka and K. Ueno, Bull. Chem. Soc. Jpn., 1987, 4067 CAS; O. Tsuge, S. Kanemasa, M. Ohe and S. Takenaka, Chem. Lett., 1986, 973 CAS.
  6. J. Mortier and M. Joucla, Tetrahedron Lett., 1987, 27, 2973; J. E. Baldwin, S. C. MacKenzie Turner and M. G. Moloney, Synlett., 1994, 925 CrossRef CAS.
  7. H. Ardill, X. L. R. Fontaine, R. Grigg, D. Henderson, J. Montgomery, V. Sridharan and S. Surendrakumar, Tetrahedron, 1990, 46, 6449 CrossRef CAS.
  8. E. Vedejs, S. Larsen and F. G. West, J. Org. Chem., 1985, 50, 2170 CrossRef CAS; E. Vedejs and F. G. West, Chem. Rev., 1986, 86, 941 CrossRef CAS.
  9. R. C. F. Jones, J. R. Nichols and M. T. Cox, Tetrahedron Lett., 1990, 31, 2333 CrossRef CAS.
  10. R. N. Butler, D. M. Farrell and C. S. Pyne, J. Chem. Res. (S), 1996, 418 Search PubMed.
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