An Efficient Catalytic Chromium-Mediated Iodocyclopropanation Reaction: Stereoselective Synthesis of Iodocyclopropanecarboxamides

Abstract

A catalytic chromium-mediated novel synthesis of iodocyclopropanecarboxamides is reported. This reaction can be carried out on aromatic (E)- or (Z)-α,β-unsaturated amides in which the C[DOUBLE BOND]C double bond is di- or trisubstituted. This process takes place with total stereospecificity and the new C[BOND]I stereogenic center is generated with high stereoselectivity. Some synthetic applications of the obtained iodocyclopropanecarboxamides are also reported. The structures of the iodocyclopropanes and derivatives were established by X-ray analysis.