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• W3113012321 startingPage "236" @default.
• W3113012321 abstract "Catechols are part of many essential chemicals and are valuable, typically nucleophilic intermediates used in synthesis. Here we describe an unexpected transformation in which they play the role of the electrophile in a formal nucleophilic aromatic substitution. We made this discovery while studying a seven-membered dioxepin ring formation during a synthesis of the benzyltetrahydroisoquinoline (S)-cularine. We suggest a chain mechanism for this new transformation that is triggered by molecular oxygen and that propagates an electrophilic ortho-quinone." @default.
• W3113012321 created "2020-12-21" @default.
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• W3113012321 date "2020-12-16" @default.
• W3113012321 modified "2023-09-24" @default.
• W3113012321 title "Total Synthesis of (<i>S</i>)-Cularine via Nucleophilic Substitution on a Catechol" @default.
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• W3113012321 doi "https://doi.org/10.1021/acs.orglett.0c04000" @default.
• W3113012321 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/33325233" @default.
• W3113012321 hasPublicationYear "2020" @default.
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