4.7 Article

Gold-catalyzed tandem cycloisomerization of alkynyloxiranes with nucleophiles: An efficient approach to 2,5-disubstituted furans

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 349, Issue 16, Pages 2493-2498

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200700319

Keywords

alkynes; alkynyloxiranes; cycloisomerization; epoxides; furans; gold

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An efficient approach to 2,5-disubstituted furans has been developed by utilizing gold-catalyzed sequential nucleophilic attack onto metal-complexed alkynes with complete regioselectivity. The reaction proceeds efficiently under mild conditions with commercially available catalysts to afford furans in moderate to excellent yields (up to 96 %) with high diversity.

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