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Sequential Photochemical and Prins Reactions for the Diastereoselective Synthesis of Tricyclic Scaffolds
Author(s) -
Donnelly Bethan L.,
Elliott Luke D.,
Willis Christine L.,
BookerMilburn Kevin I.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201903488
Subject(s) - chemistry , cyclobutene , tricyclic , stereoselectivity , diastereomer , cyclobutanes , alkene , amine gas treating , cycloaddition , prins reaction , combinatorial chemistry , organic chemistry , ring (chemistry) , catalysis
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 sp 3 ‐rich heterocyclic scaffolds.