Synthesis 2006(16): 2760-2766  
DOI: 10.1055/s-2006-942488
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Maria Carla Marcotullio*a, Valerio Campagnaa, Silvia Sternativoa, Ferdinando Costantinob, Massimo Curinia
a Dipartimento di Chimica e Tecnologia del Farmaco, Sez, Chimica Organica-Università degli Studi, 06123 Perugia, Italy
Fax: +39(075)5855116; e-Mail: marcotu@unipg.it;
b Dipartimento di Chimica-Università degli Studi, 06123 Perugia, Italy
Further Information

Publication History

Received 25 January 2006
Publication Date:
12 July 2006 (eFirst)

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.

    References

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Compound 3 showed [α]D 24 +4.06 (c 2.15, CH2Cl2). This value is comparable with the [α] value of the same tosylamide prepared from commercial (R)-2-octyl amine by reaction with p-toluenesulfonyl chloride {[α]D 23 +5.0 (c 1.7, CH2Cl2)}.

11

CCDC reference number 292928.