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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

Author:
Kunkalkar, Rupesh A., Fernandes, Rodney A.
Source:
Chemical communications 2019 v.55 no.16 pp. 2313-2316
ISSN:
1364-548X
Subject:
Lewis acids, agonists, catalytic activity, dimerization
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.
Agid:
6312522