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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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Article information


Submitted
17 Jan 2012
Accepted
17 Feb 2012
First published
07 Mar 2012

Chem. Commun., 2012,48, 3712-3714
Article type
Communication

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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