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Synfacts 2005(3): 0293-0293  
DOI: 10.1055/s-2005-916146
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Au(III)-Catalyzed Synthesis of Polysubstituted Halofurans

Contributor(s): Victor Snieckus, Farhad Nowrouzi
A. W. Sromek, M. Rubina, V. Gevorgyan*
the University of Chicago, USA
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Publication History

Publication Date:
22 November 2005 (online)

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Siginificance

Au(III)-catalyzed selective cyclo-isomerization of haloallenyl ketones to 3-halofurans is reported. The reaction proceeds in good to excellent yields (44-97%) under mild conditions for a variety of substituted haloallenyl ketones with diverse functionalities. This method allows the synthesis of halofurans possessing hydroxymethyl and alkene functionalities, which could not be derived by known methods of furan synthesis employing electrophilic reagents. A mechanism via a halirenium intermediate and involving a 1,2-migration of halogen is proposed.