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Nucleophilic Ring-Opening of Azetidinium Ions: Insights into Regioselectivity

François Couty *, Olivier David, François Durrat, Gwilherm Evano, Sami Lakhdar, Jérome Marrot, Monica Vargas-Sanchez

*Institut Lavoisier de Versailles, UMR 8180, Université de Versailles, 45, avenue des Etats-Unis, 78035 Versailles Cedex, France, Email: coutychimie.uvsq.fr

F. Couty, O. David, F. Durrat, G. Evano, S. Lakhdar, J. Marrot, M. Vargas-Sanchez, Eur. J. Org. Chem., 2006, 3479-3490.

DOI: 10.1002/ejoc.200600200 (free Supporting Information)


Abstract

Enantiopure azetidinium salts were treated with various nucleophiles (azide anion, benzylamine, acetate anion or alkoxides) which provided interesting insights into the regioselectivity of the ring-opening process.

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Key Words

Azetidines, Azetidinium ions, Nucleophilic ring-opening, Density functional calculations, Regioselectivity, 1,3-Diamines, 1,3-Azidoamines, 1,3-Aminoalcohols


ID: J24-Y2006-2340