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Lewis acid-catalyzed annulative partial dimerization of 3-aryloxyacrylates to 4-arylchroman-2-ones: synthesis of analogues of tolterodine, RORγ inhibitors and a GPR40 agonist

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Abstract

A beguiling annulative partial dimerization of 3-aryloxyacrylates to 4-arylchroman-2-ones catalyzed by Lewis acid (BF3·OEt2) has been developed. The reaction involves two molecules of 3-aryloxyacrylate, resulting in the loss of one propiolate molecule to furnish 4-arylchroman-2-one, an important structural motif found in many natural products. This methodology has been elaborated to synthesize analogues of tolterodine, RORγ inhibitors and a GPR40 agonist.

Graphical abstract: Lewis acid-catalyzed annulative partial dimerization of 3-aryloxyacrylates to 4-arylchroman-2-ones: synthesis of analogues of tolterodine, RORγ inhibitors and a GPR40 agonist

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Publication details

The article was received on 10 Dec 2018, accepted on 29 Jan 2019 and first published on 29 Jan 2019


Article type: Communication
DOI: 10.1039/C8CC09785B
Citation: Chem. Commun., 2019, Advance Article

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    Lewis acid-catalyzed annulative partial dimerization of 3-aryloxyacrylates to 4-arylchroman-2-ones: synthesis of analogues of tolterodine, RORγ inhibitors and a GPR40 agonist

    R. A. Kunkalkar and R. A. Fernandes, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C8CC09785B

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