Copper(II)-Catalyzed [2,3]-Sigmatropic Rearrangement of N-Methyltetrahydropyridinium Ylids

A ring-contractive and highly diastereoselective [2,3]-sigmatropic rearrangement occurs when N-methyl-1,2,3,6-tetrahydropyridine is treated with sub-stoichiometric amounts of copper or rhodium salts, in the presence of ethyl diazoacetate, giving ethyl cis-N-methyl-3-ethenyl proline (4).

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Bibliographische Detailangaben
Veröffentlicht in:	Journal of organic chemistry 2003-05, Vol.68 (10), p.4083-4086
Hauptverfasser:	Heath, Peter, Roberts, Edward, Sweeney, Joseph B, Wessel, Hans Peter, Workman, James A
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Preparations and properties
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Beschreibung
Zusammenfassung:	A ring-contractive and highly diastereoselective [2,3]-sigmatropic rearrangement occurs when N-methyl-1,2,3,6-tetrahydropyridine is treated with sub-stoichiometric amounts of copper or rhodium salts, in the presence of ethyl diazoacetate, giving ethyl cis-N-methyl-3-ethenyl proline (4).
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo034147v