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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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Published in: | Organic letters 2022-12, Vol.24 (51), p.9497-9501 |
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Main Authors: | , |
Format: | Article |
Language: | English |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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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. |
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ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/acs.orglett.2c03978 |