Photoredox-catalyzed hydroxymethylation of β-ketoesters: application to the synthesis of [3.3.3] propellane lactones

Youssef Nassar; Olivier Piva

doi:10.1039/D1OB01712H

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Photoredox-catalyzed hydroxymethylation of β-ketoesters: application to the synthesis of [3.3.3] propellane lactones†

Youssef Nassar^a and Olivier Piva

*^a

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* Corresponding authors

^a Université de Lyon; CNRS; UCBL; UMR 5246 – Institut de Chimie et de Biochimie Moléculaires et Supramoléculaires, 43, Boulevard du 11 Novembre 1918–69622, Villeurbanne, France
E-mail: olivier.piva@univ-lyon1.fr

Abstract

Photoredox-catalysed hydroxymethylation of β-ketoesters substituted by an allyl subunit on the α-position afforded directly the corresponding bicyclic lactones possessing both a hydroxy group and an unsaturation. A subsequent regioselective iodoetherification led to the formation of original [3.3.3] propellane structures. Substitution of the iodine atom by various nucleophiles afforded highly functionnalized structures including triazolomethyl derivatives.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/D1OB01712H
Article type: Paper
Submitted: 31 Aug 2021
Accepted: 13 Oct 2021
First published: 13 Oct 2021

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Org. Biomol. Chem., 2021,19, 9251-9259

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Photoredox-catalyzed hydroxymethylation of β-ketoesters: application to the synthesis of [3.3.3] propellane lactones

Y. Nassar and O. Piva, Org. Biomol. Chem., 2021, 19, 9251 DOI: 10.1039/D1OB01712H

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Organic & Biomolecular Chemistry

Photoredox-catalyzed hydroxymethylation of β-ketoesters: application to the synthesis of [3.3.3] propellane lactones†

Abstract

Supplementary files

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Photoredox-catalyzed hydroxymethylation of β-ketoesters: application to the synthesis of [3.3.3] propellane lactones

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