Light-Initiated Four-Step Domino-Multicomponent Synthesis of Functionalized Alkylidenecyclobutanes - Archive ouverte HAL
Article Dans Une Revue Organic Letters Année : 2024

Light-Initiated Four-Step Domino-Multicomponent Synthesis of Functionalized Alkylidenecyclobutanes

Résumé

A four-step domino-multicomponent reaction (domino-MCR) is described for the synthesis of functionalized E-alkylidenecyclobutanes from 4-hydroxy-2-methylcyclopent-2-enone derivatives and three other simple reagents. The domino-MCR is accomplished in a single protocol, comprising a tandem photochemical [2 + 2]-cycloaddition/Norrish-I/γ-H transfer reaction followed by an acetal protection and an allylic substitution reaction. In parallel, a consecutive process has been established with distinct photochemical and nonradiative sequences. An intramolecular version of these reactions provides access to complex fused-bicyclic alkylidenecyclobutanes.
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Dates et versions

hal-04816309 , version 1 (03-12-2024)

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Xiaodan Yu, Arthur Desvals, Zong Chang, Vincent Orève, David Aitken, et al.. Light-Initiated Four-Step Domino-Multicomponent Synthesis of Functionalized Alkylidenecyclobutanes. Organic Letters, 2024, 26 (46), pp.9915-9919. ⟨10.1021/acs.orglett.4c03741⟩. ⟨hal-04816309⟩
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