title: Chiral N,N'-Dioxide-Scandium(III)-Catalyzed Asymmetric Dearomatization of 2-Naphthols through an Amination Reaction.
abstract: A catalytic asymmetric dearomatization of 2-naphthols with azodicarboxylates has been accomplished by using a N,N'-dioxide-scandium(III) complex as a chiral catalyst. A number of optically active β-naphthalenone compounds with a nitrogen-containing quaternary carbon stereocenter were obtained in up to 99 % yield and up to 99 % ee under mild reaction conditions. The reaction could be scaled up to a gram-scale with the yield and ee maintained. Based on these experiments and on previous reports, a possible transition state was proposed.
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (P. R. China).
authors.forename: Xiangjin
authors.initials: X
authors.lastname: Lian
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (P. R. China).
authors.forename: Lili
authors.initials: L
authors.lastname: Lin
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (P. R. China).
authors.forename: Guojin
authors.initials: G
authors.lastname: Wang
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (P. R. China).
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Liu
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (P. R. China). xmfeng@scu.edu.cn.
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Feng
keywords: amination reaction; asymmetric catalysis; dearomatization; naphthols; scandium