期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 348, 期 16-17, 页码 2501-2508出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200600367
关键词
alkynes; furans; gold; heterocycles; homogeneous catalysis; oxepines
A series of furyl alcohols and homofuryl alcohols was synthesized by reduction of furfurals or reaction of furyllithium compounds with epoxides and subsequent propargylation. The gold-catalyzed cycloisomerization of these products furnished dihydroisobenzofurans and isochromanes. Crystal structure analyses proved the sequence of the substituents for both classes of products. Unsaturated dicarbonyl compounds as side-products show the mechanistic relationship to the analogous platinum-catalyzed re-actions. Neither ester groups, even on the 4-position of the furan ring, nor aryl bromides hinder the catalysis by gold. In the case of a substrate with an allyl ether in the side chain, a side-product, which provides evidence for a reaction of the alkyne with an inverse regioselectivity, was observed.
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