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A New, Simple Synthesis of N-Tosyl Pyrrolidines and Piperidines

Maria Carla Marcotullio, Valerio Campagna, Silvia Sternativo, Ferdinando Costantino, Massimo Curini

*Dipartimento di Chimica e Tecnologia del Farmaco, Sez, Chimica Organica-UniversitÓ degli Studi, 06123 Perugia, Italy, Email: marcotuunipg.it

M. C. Marcotullio, V. Campagna, S. Sternativo, F. Costantino, M. Curini, Synthesis, 2006, 2760-2766.

DOI: 10.1055/s-2006-942488


Abstract

Iodocyclization of unsaturated tosylamides promoted by Oxone oxidation of KI afforded, in good yields, N-tosyl iodopyrrolidines and piperidines. A new, simple method for the conversion of alcohols to tosylamides is presented.

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Key Words

pyrrolidines, piperidines, Oxone, iodocyclization, mesylation, nucleophilic substitution, toluenesulfonamides


ID: J66-Y2006-2680