Issue 87, 2020

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

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

Supplementary files

Article information

Article type
Communication
Submitted
04 Aug 2020
Accepted
06 Oct 2020
First published
06 Oct 2020

Chem. Commun., 2020,56, 13441-13444

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, 56, 13441 DOI: 10.1039/D0CC05306F

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