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Photochemically Produced Aminocyclobutanes as Masked Dienes in Thermal Electrocyclic Cascade Reactions

Research output: Contribution to journalArticle

Original languageEnglish
Pages (from-to)1463-1466
Number of pages4
JournalOrganic Letters
Volume21
Issue number5
Early online date14 Feb 2019
DOIs
DateAccepted/In press - 17 Jan 2019
DateE-pub ahead of print - 14 Feb 2019
DatePublished (current) - 14 Feb 2019

Abstract

Cyclobutane products of a triplet sensitized enamide-alkene intramolecular [2+2] photocycloaddition have been shown to undergo fragmentation under acidic conditions. This lability has been exploited by inducing a complexity generating thermal electrocyclic cascade sequence involving the in situ formation of a cyclobutene, followed by electrocyclic ring opening, Diels-Alder cycloaddition and subsequent lactamization. This combination of excited state photochemistry and thermal elec-trocyclic cascade reactions allows simple planar molecules to be rapidly transformed into sp3 rich scaffolds.

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    Rights statement: This is the accepted author manuscript (AAM). The final published version (version of record) is available online via ACS at https://doi.org/10.1021/acs.orglett.9b00211 . Please refer to any applicable terms of use of the publisher.

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