Asymmetric Synthesis of Remotely Chiral Naphthols and Naphthylamines via Naphthoquinone Methides

generation of 2-naphthoquinone 8-methides and the corresponding aza counterparts for mild one-pot asymmetric nucleophilic addition. These processes provided rapid access to a wide range of previously less accessible remotely chiral naphthols and naphthylamines with both high efficiency and excellent enantioselectivity. Control experiment and DFT calculations provided important insights into the reaction mechanism, which likely involves two phosphoric acid molecules in the enantiodetermining transition states. This work serves as a proof of concept for the exploitation of new types of extended quinone methides as versatile intermediates for asymmetric synthesis, thus providing a new platform for the efficient construction of remote benzylic stereogenic centers of aromatic compounds.