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2 + 2 Trapping of Acyloxy-1,2-cyclohexadienes with Styrenes and Electron-Deficient Olefins

Oxygenated-1,2-cyclohexadienes and their unsubstituted counterpart can be generated under mild conditions by fluoride-induced desilylation and undergo intermolecular [2 + 2]-cycloaddition reactions with a variety of alkene traps to afford bicyclo[4.2.0]­octenes. Both styrenes and electron-deficient...

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Bibliographic Details
Published in:Organic letters 2022-12, Vol.24 (51), p.9497-9501
Main Authors: Jankovic, Christian. L., West, F. G.
Format: Article
Language:English
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Summary:Oxygenated-1,2-cyclohexadienes and their unsubstituted counterpart can be generated under mild conditions by fluoride-induced desilylation and undergo intermolecular [2 + 2]-cycloaddition reactions with a variety of alkene traps to afford bicyclo[4.2.0]­octenes. Both styrenes and electron-deficient olefins react in good conversion and with complete regioselectivity in favor of cyclobutane formation at the unsubstituted C2/C3 carbons of the C1-substituted cyclic allenes. Diastereoselectivities are modest (1.1–5.7:1) with a preference for the exo-isomer.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c03978