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Issue 11, 2016
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Gold-catalyzed construction of two adjacent quaternary stereocenters via sequential C–H functionalization and aldol annulation

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Abstract

Herein, a novel and efficient gold-catalyzed intermolecular C(sp2)–H functionalization (Friedel–Crafts alkylation) and aldol annulation strategy is presented. This cascade process allows the synthesis of a series of indanol and tetrahydronaphthalenol derivatives with two adjacent quaternary stereocenters. The attractive reaction features are the use of readily available starting materials, good diastereoselectivity, good functional-group tolerance and mild reaction conditions. Furthermore, preliminary results indicate that this transformation is amenable to enantioselectivitive synthesis with further chiral ligand screening and design.

Graphical abstract: Gold-catalyzed construction of two adjacent quaternary stereocenters via sequential C–H functionalization and aldol annulation

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The article was received on 26 Oct 2015, accepted on 01 Dec 2015 and first published on 03 Dec 2015


Article type: Communication
DOI: 10.1039/C5CC08880A
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Chem. Commun., 2016,52, 2257-2260

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    Gold-catalyzed construction of two adjacent quaternary stereocenters via sequential C–H functionalization and aldol annulation

    Z. Yu, H. Qiu, L. Liu and J. Zhang, Chem. Commun., 2016, 52, 2257
    DOI: 10.1039/C5CC08880A

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