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Enantioselective [1,3] O-to-C rearrangement: dearomatization of alkyl 2-allyloxy/benzyloxy-1/3-naphthoates catalyzed by a chiral π–Cu(II) complex

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Abstract

An unprecedented catalytic asymmetric [1,3] O-to-C rearrangement of alkyl 2-allyloxy/benzyloxy-1/3-naphthoates was realized under the catalysis of a chiral π–Cu(II) complex (1–10 mol%). This dearomatization strategy provides facile access to highly functionalized β-naphthalenone derivatives bearing an all-carbon quaternary stereogenic center in high yield with excellent enantioselectivity. The π–cation interaction between the aromatic substituent of the ligand and the Cu(II) center was proved by X-ray diffraction analysis and shown to be crucial for enantioselective control. Further preliminary mechanistic studies suggest that this intramolecular reaction proceeds through a contact ion pair intermediate.

Graphical abstract: Enantioselective [1,3] O-to-C rearrangement: dearomatization of alkyl 2-allyloxy/benzyloxy-1/3-naphthoates catalyzed by a chiral π–Cu(ii) complex

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Publication details

The article was received on 15 Dec 2018, accepted on 10 Jan 2019 and first published on 10 Jan 2019


Article type: Edge Article
DOI: 10.1039/C8SC05601C
Citation: Chem. Sci., 2019, Advance Article
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    Enantioselective [1,3] O-to-C rearrangement: dearomatization of alkyl 2-allyloxy/benzyloxy-1/3-naphthoates catalyzed by a chiral π–Cu(II) complex

    L. Yao and K. Ishihara, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C8SC05601C

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