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

Ge, Shulin; Kang, Tengfei; Lin, Lili; Zhang, Xiying; Zhao, Peng; Liu, Xiaohua; Feng, Xiaoming

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

2017

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.

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