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Synthesis of Chiral Tetrahydrofurans and Pyrrolidines by Visible‐Light‐Mediated Deoxygenation

The synthesis of chiral tetrahydrofurans and pyrrolidines starting from 1,2‐diols or β‐amino alcohols, respectively, by visible‐light‐mediated deoxygenation is described. Easily accessible monoallylated/propargylated substrates were activated either as inexpensive ethyl oxalates or as recyclable 3,5...

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Detalles Bibliográficos
Autores principales: Rackl, Daniel, Kais, Viktor, Lutsker, Eugen, Reiser, and Oliver
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5412674/
https://www.ncbi.nlm.nih.gov/pubmed/28529446
http://dx.doi.org/10.1002/ejoc.201700014
Descripción
Sumario:The synthesis of chiral tetrahydrofurans and pyrrolidines starting from 1,2‐diols or β‐amino alcohols, respectively, by visible‐light‐mediated deoxygenation is described. Easily accessible monoallylated/propargylated substrates were activated either as inexpensive ethyl oxalates or as recyclable 3,5‐bis(trifluoromethyl)benzoates to generate alkyl radicals suitable for 5‐exo‐trig/5‐exo‐dig cyclizations under visible‐light irradiation.