Cis -2,3-disubstituted cyclopropane 1,1-diesters in [3 + 2] annulations with aldehydes: Highly diastereoselective construction of densely substituted tetrahydrofurans

摘要

A series of cis-2,3-disubstituted cyclopropane 1,1-diesters were examined in the AlCl_3-promoted [3 + 2]-annulations with aldehydes. In this reaction, these cis-cyclopropanes displayed reactivities starkly different from their trans counterparts in terms of the high chemical yields (up to 98%) and provided the desired annulation products with excellent diastereomeric purity. This protocol provides a facile and highly stereoselective way to construct synthetically useful pentasubstituted tetrahydrofurans not easily accessible using other methods.