Alpha-cyclization of Tertiary-amines .3. Captodative Or Push-pull Enamines Form Pyrrolines, Pyrrolizidines and Their Ring Homologs With Dimethyl Acetylenedicarboxylate in a Highly Diastereoselective Reaction

Deboeck, B.;Jiang, SP.;Janousek, Z.;Viehe, HG.
(1994) Tetrahedron — Vol. 50, n° 24, p. 7075-7092 (1994)

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Authors
  • Deboeck, B.
    Author
  • Jiang, SP.
    Author
  • Janousek, Z.
    Author
  • Viehe, HG.
    Author
Abstract
The title one-pot reaction occurs through a sequence of [2+2] cycloaddition ring opening to dienamines and formation of a 1,5-dipole by [1,6] hydrogen-shift. This intermediate may cyclize or in sterically suitable cases and at lower temperatures, lead to isolable N-vinyl enamines by proton transfer.
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Deboeck, B., Jiang, SP., Janousek, Z., & Viehe, HG. (1994). Alpha-cyclization of Tertiary-amines .3. Captodative Or Push-pull Enamines Form Pyrrolines, Pyrrolizidines and Their Ring Homologs With Dimethyl Acetylenedicarboxylate in a Highly Diastereoselective Reaction. Tetrahedron, 50(24), 7075-7092. https://doi.org/10.1016/S0040-4020(01)85235-2 (Original work published 1994)