Highly diastereoselective synthesis of tetrahydrofurans via Lewis acid-catalyzed cyclopropane/aldehyde cycloadditions.
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.
Pohlhaus
Patrick D
PD
Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290, USA.
Johnson
Jeffrey S
JS