Low-Temperature Heck Reactions of Axially Chiral o-Iodoacrylanilides Occur with Chirality Transfer: Implications for Catalytic Asymmetric Heck Reactions

Low-temperature Heck reactions of chiral o -iodoacrylanilides with achiral palladium catalysts occur with efficient transfer of chirality from the chiral axis of the precursor to the new stereocenter of the product. The results suggest that the primary stereocontrolling step in asymmetric Heck reactions is a dynamic kinetic resolution (oxidative addition to the C−I) bond and not a face selective reaction (complexation or insertion to the alkene).