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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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:
Full Papers
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
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author Rackl, Daniel
Kais, Viktor
Lutsker, Eugen
Reiser, and Oliver
author_facet Rackl, Daniel
Kais, Viktor
Lutsker, Eugen
Reiser, and Oliver
author_sort Rackl, Daniel
collection PubMed
description 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.
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spelling pubmed-54126742017-05-19 Synthesis of Chiral Tetrahydrofurans and Pyrrolidines by Visible‐Light‐Mediated Deoxygenation Rackl, Daniel Kais, Viktor Lutsker, Eugen Reiser, and Oliver European J Org Chem Full Papers 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. John Wiley and Sons Inc. 2017-02-28 2017-04-18 /pmc/articles/PMC5412674/ /pubmed/28529446 http://dx.doi.org/10.1002/ejoc.201700014 Text en © 2017 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs (http://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Full Papers
Rackl, Daniel
Kais, Viktor
Lutsker, Eugen
Reiser, and Oliver
Synthesis of Chiral Tetrahydrofurans and Pyrrolidines by Visible‐Light‐Mediated Deoxygenation
title Synthesis of Chiral Tetrahydrofurans and Pyrrolidines by Visible‐Light‐Mediated Deoxygenation
title_full Synthesis of Chiral Tetrahydrofurans and Pyrrolidines by Visible‐Light‐Mediated Deoxygenation
title_fullStr Synthesis of Chiral Tetrahydrofurans and Pyrrolidines by Visible‐Light‐Mediated Deoxygenation
title_full_unstemmed Synthesis of Chiral Tetrahydrofurans and Pyrrolidines by Visible‐Light‐Mediated Deoxygenation
title_short Synthesis of Chiral Tetrahydrofurans and Pyrrolidines by Visible‐Light‐Mediated Deoxygenation
title_sort synthesis of chiral tetrahydrofurans and pyrrolidines by visible‐light‐mediated deoxygenation
topic Full Papers
url 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
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