N,N‘-Carbonyldiimidazole-Mediated Cyclization of Amino Alcohols to Substituted Azetidines and Other N-Heterocycles

Renata Marcia de Figueiredo,† Roland Fröhlich,‡ and Mathias Christmann*†
Institut fr Organische Chemie der RWTH Aachen, Landoltweg 1, 52074 Aachen, Germany, and Organisch-Chemisches Institut der Universitt Mnster, Corrensstrasse 40, 48149 Mnster, Germany
J. Org. Chem., 2006, 71 (11), pp 4147–4154
DOI: 10.1021/jo060130b
Publication Date (Web): April 22, 2006
Copyright © 2006 American Chemical Society
†

 Institut für Organische Chemie der RWTH Aachen.

,
‡

 Organisch-Chemisches Institut, Universität Münster.

,
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, christmann@oc.rwth-aachen.de

Abstract

Abstract Image

Amino alcohols are important synthons for N-heterocycles. We have developed an efficient method to activate hydroxyl groups, which avoids the use of toxic reagents and tolerates a wide variety of functional groups. Our strategy has been applied to the synthesis of functionalized p-methoxyphenyl-protected azetidines, pyrrolidines, and piperidines. The required amino alcohols were synthesized according to an optimized proline-catalyzed Mannich protocol. An azetidine analogue of ezetimibe was synthesized to demonstrate the potential for the synthesis of drug-like molecules.

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History

  • Published In Issue May 26, 2006
  • Received January 20, 2006

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