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Synthesis 2019; 51(16): 3151-3159
DOI: 10.1055/s-0037-1611820
DOI: 10.1055/s-0037-1611820
paper
Organocatalytic Gram-Scale Synthesis and Alkylation of Heteroaryl and Electron-Rich Aryl α-Substituted γ-Lactones
We gratefully thank the Agence Nationale de la Recherche for financial support (HFOrgCat project ANR JCJC: ANR-12-JS07-0009).Further Information
Publication History
Received: 28 February 2019
Accepted after revision: 09 April 2019
Publication Date:
30 April 2019 (online)
Abstract
The synthesis of γ-lactones α-substituted with heterocycles and electron-rich aromatic rings is described. The method, based on a sequence involving an organocatalytic addition of boronic acid to the 5-hydroxyfuran-2(5H)-one, followed by reduction and lactonization, gives access to broad range of γ-lactones on a gram scale. Among these, γ-lactones bearing a benzofuran, a benzothiophene, and an indole ring were alkylated in mild catalytic conditions to construct α-quaternary stereocenters. Interesting mild oxidation reaction, using molecular oxygen, was also highlighted during this study.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611820. Included are copies of NMR spectra of all new compounds and ORTEP representations of 26a (CCDC 1898999) and 26b (CCDC 1899000).
- Supporting Information
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