Synfacts 2011(8): 0833-0833  
DOI: 10.1055/s-0030-1260856
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

AuCl3-Catalyzed Synthesis of 5-Bromomethyl Oxazoles from Amino Acids

Contributor(s): Victor Snieckus, Johnathan Board
C. L. Paradise, P. R. Sarkar, M. Razzak, J. K. De Brabander*
The University of Texas Southwestern Medical Center at Dallas, USA
Further Information

Publication History

Publication Date:
20 July 2011 (online)


Reported is the one-pot synthesis of 5-bromomethyl oxazoles by sequential gold(III)-catalyzed cyclization of amino acid derived propargyl amides to form intermediate A, followed by bromination to give the observed products in good yield. This work builds upon the results of Hashmi who developed the AuCl3-catalyzed cyclization to form oxazoles from amides (e.g., A. S. K. Hashmi., J. P. Weyrauch, W. Frey, J. W. Bats Org. Lett. 2004, 6, 4391). However, both Hashmi and the current authors found the reaction fails when non-terminal alkynes are used. The present method overcomes this limitation by intercepting a reactive intermediate (observed using ¹H NMR spectroscopy during the cyclization by the Hashmi group) to form a reactive bromide.