期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 27, 页码 9095-9098出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201903488
关键词
cyclobutene; fluorination; photochemistry; Prins cyclization; Ritter reaction
资金
- EPSRC [EP/L015366/1, EP/P013341/1]
- AstraZeneca
- University of Bristol
- Bristol Chemical Synthesis Centre for Doctoral Training
- EPSRC [EP/P013341/1, EP/L003325/1] Funding Source: UKRI
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.
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