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Highly Diastereoselective Synthesis of Tetrahydrofurans via Lewis Acid-Catalyzed Cyclopropane/Aldehyde Cycloadditions

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journal contribution
posted on 2005-02-04, 00:00 authored by Patrick D. Pohlhaus, Jeffrey S. Johnson
A one-step procedure for the preparation of 2,5-disubstituted tetrahydrofurans from donor−acceptor cyclopropanes and aldehydes has been developed. In the presence of a catalytic amount of Sn(OTf)2, cyclopropanes bearing an aryl or conjugated donor substituent vicinal to a malonyl diester group undergo cycloadditions with diverse conjugated aldehydes furnishing tetrahydrofurans with high cis diastereoselectivity. This method is useful for the preparation of regiodefined tetrahydrofurans.