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

Autor:	Bethan L. Donnelly, Luke D. Elliott, Kevin I. Booker-Milburn, Christine L. Willis
Rok vydání:	2019
Předmět:	Cyclobutene cyclobutene 010402 general chemistry 01 natural sciences Catalysis BCS and TECS CDTs chemistry.chemical_compound flourination Organic chemistry Amine derivatives chemistry.chemical_classification photochemistry Prins cyclisation 010405 organic chemistry Alkene Diastereomer General Chemistry General Medicine Prins reaction Ritter reaction 0104 chemical sciences chemistry Stereoselectivity ritter reaction Tricyclic
Zdroj:	Donnelly, B, Elliott, L, Willis, C & Booker-Milburn, K 2019, ' Sequential Photochemical and Prins Reactions for the Diastereoselective Synthesis of Tricyclic Scaffolds ', Angewandte Chemie-International Edition, vol. 58, no. 27, pp. 9095-9098 . https://doi.org/10.1002/anie.201903488
ISSN:	1521-3757 0044-8249
DOI:	10.1002/ange.201903488
Popis:	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.
Databáze:	OpenAIRE
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