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Organocatalytic Gram-Scale Synthesis and Alkylation of Heteroaryl and Electron-Rich Aryl α-Substituted γ-Lactones

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.
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https://hal.univ-reims.fr/hal-02429308
Contributor : Emmanuel Riguet Connect in order to contact the contributor
Submitted on : Monday, January 6, 2020 - 3:30:14 PM
Last modification on : Tuesday, January 4, 2022 - 6:08:28 AM

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Maxence Bos, Floris Buttard, Alexis Vallée, Emmanuel Riguet. Organocatalytic Gram-Scale Synthesis and Alkylation of Heteroaryl and Electron-Rich Aryl α-Substituted γ-Lactones. SYNTHESIS, Georg Thieme Verlag, 2019, 51 (16), pp.3151-3159. ⟨10.1055/s-0037-1611820⟩. ⟨hal-02429308⟩

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