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Cationic Gold‐ and Silver‐Catalyzed Cycloisomerizations of Propargylic Ureas: A Selective Entry to Oxazolidin‐2‐imines and Imidazolidin‐2‐ones

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Abstract:

Abstract

A comparative study on transition metal‐catalyzed cycloisomerizations of propargylic ureas derived in situ from secondary propargylic amines and tosyl isocyanate was performed. The influence of catalytic system on the reaction outcome was thoroughly studied on two model examples resulting in the establishment of two selective protocols for both O‐ and N‐cyclizations. The application of cationic gold(I) catalysis generally resulted in a formation of oxazolidin‐2‐imines as major products while the application of silver(I) triflate selectively provided the corresponding imidazolidin‐2‐ones. An attempt to rationalize the observed chemoselectivity is described. The scope of both processes was demonstrated through the use of variously substituted secondary propargylic amines.

Document Type: Research Article

DOI: https://doi.org/10.1002/adsc.201200905

Affiliations: 1: Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, B-3001 Leuven, Belgium, Fax: (+32)-16-32-79-90 2: Biomolecular Architecture, Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, B-3001 Leuven, Belgium

Publication date: 2013-03-11

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