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Issue 27, 2014
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Lewis acid promoted C–C and copper-catalyzed C–O bond formation: synthesis of neoflavans

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Abstract

An intramolecular [Cu]-catalyzed C–O bond formation for the synthesis of neoflavans is presented. Lewis acid promoted Friedel–Crafts Michael addition of electron rich aromatic systems onto the double bond of the cinnamate ester was employed to furnish a β-diaryl ester. Electrophilic aromatic bromination of the β-diaryl ester and reduction/Grignard addition furnished the required precursor alcohols. The method is applicable to the synthesis of neoflavans containing tertiary as well as quaternary carbon centers. Significantly, the neoflavan substructures are present in biologically active compounds.

Graphical abstract: Lewis acid promoted C–C and copper-catalyzed C–O bond formation: synthesis of neoflavans

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Supplementary files

Article information


Submitted
03 Jan 2014
Accepted
30 Jan 2014
First published
31 Jan 2014

This article is Open Access

RSC Adv., 2014,4, 13941-13945
Article type
Communication
Author version available

Lewis acid promoted C–C and copper-catalyzed C–O bond formation: synthesis of neoflavans

B. Suchand, J. Krishna, K. Mritunjoy and G. Satyanarayana, RSC Adv., 2014, 4, 13941
DOI: 10.1039/C4RA00048J

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