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Issue 31, 2012
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Catalytic asymmetric synthesis of chromenes and tetrahydroquinolines via sequential allylic alkylation and intramolecular Heck coupling

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Abstract

Highly enantioselective synthesis of chiral chromenes and tetrahydroquinolines is achieved by combining asymmetric copper-catalyzed allylic substitution with Grignard reagents and an efficient intramolecular Heck reaction. Moreover, the exocyclic double bond formed in the cyclisation was subjected to RCM, hydroboration and hydrogenation illuminating the synthetic versatility of these heterocycles.

Graphical abstract: Catalytic asymmetric synthesis of chromenes and tetrahydroquinolines via sequential allylic alkylation and intramolecular Heck coupling

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Publication details

The article was received on 17 Jan 2012, accepted on 17 Feb 2012 and first published on 07 Mar 2012


Article type: Communication
DOI: 10.1039/C2CC30395G
Chem. Commun., 2012,48, 3712-3714

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    Catalytic asymmetric synthesis of chromenes and tetrahydroquinolines via sequential allylic alkylation and intramolecular Heck coupling

    V. Hornillos, A. W. van Zijl and B. L. Feringa, Chem. Commun., 2012, 48, 3712
    DOI: 10.1039/C2CC30395G

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