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Sequential Photochemical and Prins Reactions for the Diastereoselective Synthesis of Tricyclic Scaffolds

Research output: Contribution to journalArticle

Original languageEnglish
Number of pages5
JournalAngewandte Chemie - International Edition
Early online date24 May 2019
DOIs
DateAccepted/In press - 26 Apr 2019
DateE-pub ahead of print - 24 May 2019
DatePublished (current) - 24 May 2019

Abstract

Cyclobutene alcohols undergo Prins cyclisations to generate single diastereomers of novel tricyclic heterocycles with five contiguous stereocentres. The reaction times are significantly shorter (ca. 15 min) than with traditional alkene substrates. Stereoselective aza-Prins cyclisations of cyclobutene amine derivatives give fused aza-heterocyclic scaffolds. Computational studies provide insight into the observed stereocontrol. The modular approach is flexible, enabling the introduction of a variety of functional groups (including amides, nitriles, alkynes, and arenes) into the sp3-rich heterocyclic scaffolds.

    Research areas

  • cyclobutene, flourination, photochemistry, Prins cyclisation, ritter reaction

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  • Full-text PDF (accepted author manuscript)

    Rights statement: This is the author accepted manuscript (AAM). The final published version (version of record) is available online via Wiley at https://onlinelibrary.wiley.com/doi/10.1002/anie.201903488. Please refer to any applicable terms of use of the publisher.

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    Embargo ends: 29/04/20

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