Lewis-Acid-Catalysed tandem meinwald rearrangement/Intermolecular [3+2]- Cycloaddition of epoxides with Donor–acceptor cyclopropanes: Synthesis of functionalized tetrahydrofurans

Abstract

A Lewis-acid-catalysed tandem Meinwald rearrangement/[3+2]-cycloaddition of epoxides with donor-acceptor cyclopropanes to synthesize varieties of cis-2,5-aryl-benzyl-substituted tetrahydrofurans is described. An enantioselective version of the same transformation was achieved using an InCl3-PyBOX catalyst system. A Lewis-acid-catalysed tandem Meinwald rearrangement/[3+2]-cycloaddition of epoxides with donor-acceptor cyclopropanes to synthesize varieties of cis-2,5-aryl-benzyl-substituted tetrahydrofurans is described. An enantioselective version of the same transformation is also presented using various BOX ligands.