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Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives.

ABSTRACT: An enantioselective hydroxylative dearomatization of 2-naphthols with oxaziridines has been accomplished using a N,N'-dioxide-scandium(iii) complex catalyst. Various substituted ortho-quinols could be obtained in high yields (up to 99%) and enantioselectivities (up to 95?:?5 er). This methodology could be applied in the synthesis of bioactive lacinilenes in a gram-scale reaction. Based on the experimental investigations and previous work, a possible catalytic model was proposed.

SUBMITTER: Zhang Y

PROVIDER: S-EPMC5625263 | biostudies-literature | 2017 Sep

REPOSITORIES: biostudies-literature

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Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives.

Zhang Yu Y Liao Yuting Y Liu Xiaohua X Xu Xi X Lin Lili L Feng Xiaoming X

Chemical science 20170724 9

An enantioselective hydroxylative dearomatization of 2-naphthols with oxaziridines has been accomplished using a N,N'-dioxide-scandium(iii) complex catalyst. Various substituted ortho-quinols could be obtained in high yields (up to 99%) and enantioselectivities (up to 95 : 5 er). This methodology could be applied in the synthesis of bioactive lacinilenes in a gram-scale reaction. Based on the experimental investigations and previous work, a possible catalytic model was propo ...[more]

PMID: 28989691

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