Remote asymmetric conjugate addition of naphthoquinone methides: constructing adjacent tertiary-quaternary carbon stereocenters

Abstract

The asymmetric reactions of naphthoquinone methides having carbonyl and methide units on different rings have remained underdeveloped due to the challenging remote stereoselectivity control. Herein, the asymmetric conjugate addition of in situ-generated naphthoquinone methides to β-ketoesters has been developed, in the presence of a chiral bis(oxazoline)-Cu(II) complex, providing various naphthol skeletons bearing adjacent tertiary-quaternary carbon stereocenters in high yields and enantioselectivities.