Photoinduced Radical-Polar Crossover Cyclization for the Synthesis of α-Exo-Alkenyl γ-Lactones

α-Exoalkenyl γ-lactone skeletons are of great significance due to their synthetic challenges and the diverse biological properties exhibited by numerous natural and synthetic molecules. In this work, we developed an alternative method for the synthesis of α-exoalkenyl γ-lactones via visible light-induced radical-polar crossover cyclization (RPCC) reaction. These reactions proceed under mild photochemical conditions in the presence of fluorescein sodium as photocatalyst, yielding structurally diverse γ-lactones conveniently, while demonstrating good functional group tolerance and a broad substrate scope. Furthermore, a plausible RPCC mechanistic pathway is proposed based on control experiments.

Authors

Institutions

Publication Details

Journal
Organic Letters
Published
2025-11-25
DOI
https://doi.org/10.1021/acs.orglett.5c04424
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.00
Controls
|||
ALL TIME
JAN
FEB
MAR
APR
MAY
JUN
JUL
AUG
SEP
OCT
article

Photoinduced Radical-Polar Crossover Cyclization for the Synthesis of α-Exo-Alkenyl γ-Lactones

Chao Shu, Xinke Ouyang, Jia Yu, Zhiming Zhu et al.
Organic Letters
Radical Photochemical Reactions
article

Photoinduced Radical-Polar Crossover Cyclization for the Synthesis of α-Exo-Alkenyl γ-Lactones

Chao Shu, Xinke Ouyang, Jia Yu, Zhiming Zhu, Xiaoyu Liu
article en

Abstract

α-Exoalkenyl γ-lactone skeletons are of great significance due to their synthetic challenges and the diverse biological properties exhibited by numerous natural and synthetic molecules. In this work, we developed an alternative method for the synthesis of α-exoalkenyl γ-lactones via visible light-induced radical-polar crossover cyclization (RPCC) reaction. These reactions proceed under mild photochemical conditions in the presence of fluorescein sodium as photocatalyst, yielding structurally diverse γ-lactones conveniently, while demonstrating good functional group tolerance and a broad substrate scope. Furthermore, a plausible RPCC mechanistic pathway is proposed based on control experiments.

Organic LettersVol. 27(49)
Central China Normal University (CN), Ministry of Education (ME)
Openalex Percentile: Top 73%
Radical Photochemical Reactions
AI Navigator

Ask Laika to Summarize, Analyze, and Connect papers live on the map.

Summarize Papers & Methodologies

Extract key findings, datasets, and comparative methods across publications.

Benchmark Rankings & Visual Analytics

Rank top research institutions, authors, funders, topics, and journals by Field-Weighted Citation Impact (FWCI) and paper volume with instant charts.

Connect Distant Disciplines

Bridge topological clusters on the map to find hidden collaborative intersections.