Stereoselective Route to 2,3,4,5-Tetraaryltetrahydrofurans via Efficient Cascade Synthesis of 2,3-Dihydrofurans with Four Different (Hetero)Aryl Substituents

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 24, 2025

Tf2NH-mediated regio- and diastereoselective skeletal metamorphosis of 1-alkynyl-2,3-diaryl-2-methoxycarbonylcyclopropyl ketones readily gave 2,3,4,5-tetraaryl-2,3-dihydrofurans. Controllable reduction removal the ester group then precisely afforded four types eight possible tetrahydrofuran (THF) diastereomers with different (hetero)aryl substituents. Further, deuterium-labeling results revealed an unprecedented hydrogen transfer from formyl C-H bond in tBuOK-promoted decarbonylation under tBuOH-free conditions.

Language: Английский

Switchable skeletal editing of quinolines enabled by cyclizative sequential rearrangements

Nature Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 7, 2025

Language: Английский