Isomérisation cis-trans en Série Alkyl-4-vinyl-3-pipéridine par Sigmatropie [3.3]. Synthèse des Epivinyl Isomères des Alcaloïdes du Quinquina |
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| Authors: | Gérard Engler Henri Strub Jean-Pierre Fleury Hans Fritz |
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| Institution: | 1. Laboratoire de Synthèse et de Photochimie Organiques (Laboratoire Associé au CNRS), Ecole Nationale Supéricure de Chimie de Mulhouse, F-68093 Mulhouse Cedex;2. Ciba-Geigy, CH–4002 Bâle |
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| Abstract: | cis, trans Isomerization of 4-Alkyl-3-vinylpiperidines by 3.3] Sigmatropic Rearrangement. Synthesis of Epivinyl Isomers of Cinchona Alkaloids Isomerization of 4-alkyl-3-vinylpiperidines induced by formaldehyde has been studied for ethyl meroquinate and quinotoxine. The equilibration of cis- and trans-isomers occurs by involvement of a 3.3] sigmatropic rearrangement. This process permits an easy access to the trans-isomers from natural products of cis-configuration and has been used to obtain the epivinyl isomers of cinchona alkaloids. |
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