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Isomérisation cis ‐ trans en Série Alkyl‐4‐vinyl‐3‐pipéridine par Sigmatropie [3.3]. Synthèse des Epivinyl Isomères des Alcaloïdes du Quinquina
Author(s) -
Engler Gérard,
Strub Henri,
Fleury JeanPierre,
Fritz Hans
Publication year - 1985
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19850680329
Subject(s) - chemistry , isomerization , alkyl , cinchona , sigmatropic reaction , cis–trans isomerism , stereochemistry , medicinal chemistry , organic chemistry , catalysis , enantioselective synthesis
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.