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

Chemical Science Pub Date: 2017-07-24 DOI: 10.1039/C7SC02809A

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.

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