Catalytic Asymmetric Allylic Substitution/Isomerization with Central Chirality Transposition

Abstract

We have developed a catalytic asymmetric allylic substitution/isomerization process with central chirality transposition. This process takes advantage of the ambident reactivity of the 2-indole imine methide generated <i>in situ</i> from racemic tertiary indolylmethanols. The use of a suitable chiral phosphoric acid catalyst and an <i>ortho</i>-directing group allowed regioselective formation a C-C bond at the 3 position but enantiocontrolled construction of a stereogenic center at the 2-benzylic position.