Redox-Tag-Guided Radical Cation Diels –Alder Reactions: Use of Enol Ethers as Dienophiles

Synlett DOI: 10.1055/a-2161-9607 Although radical cation Diels–Alder reactions enable the formation of cyclohexene ring systems between electronically mismatched (both electron-rich) dienes and dienophiles, which is otherwise difficult or impossible to achieve under thermal conditions, the substrate scope has been limited. Herein, we disclose that a radical cation Diels–Alder reaction using an enol ether as an electron-rich (and therefore oxidizable) dienophile is possible through a rationally designed redox tag strategy. Electrochemical and TiO2 photochemical approaches are effective in driving the reaction, where both intermolecular and intramolecular electron transfers are the key. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text

Source: Synlett - October 23, 2023 Category: Chemistry Authors: Morizumi, Haruka Nakayama, Kaii Kitano, Yoshikazu Okada, Yohei Tags: cluster Source Type: research