Enantioselective synthesis of tetrahydrofuran derivatives by sequential henry reaction and iodocyclization of γ,δ-unsaturated alcohols

Abstract

A sequential one-pot Cu-catalyzed asymmetric Henry reaction and iodocyclization is disclosed. The transformation provides efficient access to biologically and synthetically useful 2,2,5-trisubstituted tetrahydrofuran derivatives. The combination of Cu(OAc)2·H2O with a novel chiral sulfoxide-Schiff base hybrid ligand under mild reaction conditions tolerates a wide range of 4-substituted γ,δ-unsaturated aldehydes, and the subsequent iodocyclization furnishes the corresponding products in generally high yields with excellent enantioselectivities. The products can be easily converted into amines with excellent diastereo- and enantioselectivities. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.