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Photoinduced umpolung addition of carbonyl compounds with α,β-unsaturated esters enables the polysubstituted γ-lactone formation

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Abstract

We herein report the photoinduced intermolecular umpolung addition of aromatic ketones/aldehydes with α,β-unsaturated esters via ketyl radical intermediates. Following an intramolecular transesterification, a variety of γ-lactone derivatives are readily accessed. Mechanistic investigations demonstrate the significant role of Hantzsch ester, which serves both as the electron and proton donor.

Graphical abstract: Photoinduced umpolung addition of carbonyl compounds with α,β-unsaturated esters enables the polysubstituted γ-lactone formation

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Article information


Submitted
04 Aug 2020
Accepted
06 Oct 2020
First published
06 Oct 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Photoinduced umpolung addition of carbonyl compounds with α,β-unsaturated esters enables the polysubstituted γ-lactone formation

J. Gu, W. Zhang, S. R. Jackson, Y. He and Z. Guan, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC05306F

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