Asymmetric catalytic [4+3] cycloaddition of ortho-quinone methides with oxiranes

Abstract

Catalytic enantioselective [4+3] cycloaddition reaction between o-quinone methides and oxiranes was achieved by using a chiral N,N′-dioxide/Tb^III complex as the catalyst, affording medium-sized hydrodioxepine derivatives in high yields (up to 99%) with good to excellent diastereo-(up to 94 : 6 dr) and enantioselectivities (up to 97% ee). The topographic steric maps and distribution of the buried volume (% V_Bur) of the catalysts via Cavallo's SambVca 2 tool were collected to effectively represent the chiral pocket of metal complexes of chiral N,N′-dioxides.