Chiral N,N′-dioxide/Sc(OTf)₃complex-catalyzed asymmetric dearomatization of β-naphthols

Abstract

An efficient N,N'-dioxide-scandium(iii) complex catalytic system has been developed for the asymmetric dearomatization of β-naphthols through conjugate addition to alkynones. A variety of Z-predominated β-naphthalenone compounds were obtained in moderate to high yields with excellent enantioselectivities (up to 98% ee). Moreover, a possible transition state was proposed to explain the origin of the stereoselectivity.