Amino Zinc Enolate Carbocyclization Reactions. New Access to Polysubstituted Piperidine Derivatives.
Various N-pent-4-enylglycine methyl esters have been submitted to carbocyclization of their zinc enolates onto the unactivated double bond. The cyclization to substituted pipecolic esters is highly stereoselective. In most cases, substitution of the pent-4-enyl moiety on various sites leads to a single isomer, hence a way to di-, tri-, tetra-, or pentasubstituted piperidines.
Lorthiois
Edwige
E
Laboratoire de Chimie des Organoéléments, Université P. et M. Curie, 4 Place Jussieu, 75252 Paris Cedex 05-France.
Marek
Ilane
I
Normant
Jean F.
JF