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.
Original language | English |
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Pages (from-to) | 9095-9098 |
Number of pages | 4 |
Journal | Angewandte Chemie - International Edition |
Volume | 58 |
Issue number | 27 |
Early online date | 24 May 2019 |
DOIs | |
Publication status | Published - 24 Jun 2019 |
Structured keywords
- BCS and TECS CDTs
Keywords
- cyclobutene
- flourination
- photochemistry
- Prins cyclisation
- ritter reaction
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Dive into the research topics of 'Sequential Photochemical and Prins Reactions for the Diastereoselective Synthesis of Tricyclic Scaffolds'. Together they form a unique fingerprint.Student theses
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[2+2]-Photocycloaddition Reactions in the Synthesis of Novel Scaffolds and Natural Products
Author: Donnelly, B., 11 May 2021Supervisor: Willis, C. (Supervisor) & Booker-Milburn, K. I. (Supervisor)
Student thesis: Doctoral Thesis › Doctor of Philosophy (PhD)
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