X-ray-analysis of Pyrrolizidines Synthesized By Diastereoselective Alpha-cyclization of Captodative Or Push-pull Enamines With Dimethyl Acetylenedicarboxylate

Tinant, Bernard;Declercq, Jean-Paul;Feneau-Dupont, J.;Deboeck, B.;Viehe, HG.;et.al.
(1995) Societes Chimiques Belges. Bulletin — Vol. 104, n° 6, p. 397-400 (1995)

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  • Tinant, BernardUCLouvain
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  • Declercq, Jean-PaulUCLouvain
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  • Feneau-Dupont, J.UCLouvain
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  • Deboeck, B.
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  • Viehe, HG.
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Abstract
The title reactions lead to unique diastereoisomers of pyrrolizidines 1a [dimethyl 2,3-dehydro-1-methyl-3-cyanopyrrolizidine-1,2-dicarboxylate] or 1b [dimethyl 2,3-dehydro-1-(ethoxycarbonylmethyl)1-3-phenyl-pyrrolizidine-1,2-dicarboxylate] with relative stereochemistry (1a: trans; 1b: cis) established by X-ray diffraction analysis. The heterocycle adopts a different conformation in 1a and 1b.
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Tinant, B., Declercq, J.-P., Feneau-Dupont, J., Deboeck, B., Jiang, S., Janousek, Z., & Viehe, HG. (1995). X-ray-analysis of Pyrrolizidines Synthesized By Diastereoselective Alpha-cyclization of Captodative Or Push-pull Enamines With Dimethyl Acetylenedicarboxylate. Societes Chimiques Belges. Bulletin, 104(6), 397-400. https://doi.org/10.1002/bscb.19951040607 (Original work published 1995)