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

Author:
Ge, Shulin, Kang, Tengfei, Lin, Lili, Zhang, Xiying, Zhao, Peng, Liu, Xiaohua, Feng, Xiaoming
Source:
Chemical communications 2017 v.53 no.86 pp. 11759-11762
ISSN:
1364-548X
Subject:
chemical compounds, chemical reactions, enantioselectivity
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.
Agid:
6396699