Towards Enantiomerically Pure Unnatural α-Amino Acids via Photoredox Catalytic 1,4-Additions to a Chiral Dehydroalanine

[Image: see text] Chemo- and diastereoselective 1,4-conjugate additions of anionic and radical C-nucleophiles to a chiral bicyclic dehydroalanine (Dha) are described. Of particular importance, radical carbon photolysis by a catalytic photoredox process using a simple method with a metal-free photoca...

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Autores principales: Oroz, Paula, Navo, Claudio D., Avenoza, Alberto, Busto, Jesús H., Corzana, Francisco, Jiménez-Osés, Gonzalo, Peregrina, Jesús M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9639051/
https://www.ncbi.nlm.nih.gov/pubmed/36179039
http://dx.doi.org/10.1021/acs.joc.2c01774
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author Oroz, Paula
Navo, Claudio D.
Avenoza, Alberto
Busto, Jesús H.
Corzana, Francisco
Jiménez-Osés, Gonzalo
Peregrina, Jesús M.
author_facet Oroz, Paula
Navo, Claudio D.
Avenoza, Alberto
Busto, Jesús H.
Corzana, Francisco
Jiménez-Osés, Gonzalo
Peregrina, Jesús M.
author_sort Oroz, Paula
collection PubMed
description [Image: see text] Chemo- and diastereoselective 1,4-conjugate additions of anionic and radical C-nucleophiles to a chiral bicyclic dehydroalanine (Dha) are described. Of particular importance, radical carbon photolysis by a catalytic photoredox process using a simple method with a metal-free photocatalyst provides exceptional yields and selectivities at room temperature. Moreover, these 1,4-conjugate additions offer an excellent starting point for synthesizing enantiomerically pure carbon-β-substituted unnatural α-amino acids (UAAs), which could have a high potential for applications in chemical biology.
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spelling pubmed-96390512022-11-08 Towards Enantiomerically Pure Unnatural α-Amino Acids via Photoredox Catalytic 1,4-Additions to a Chiral Dehydroalanine Oroz, Paula Navo, Claudio D. Avenoza, Alberto Busto, Jesús H. Corzana, Francisco Jiménez-Osés, Gonzalo Peregrina, Jesús M. J Org Chem [Image: see text] Chemo- and diastereoselective 1,4-conjugate additions of anionic and radical C-nucleophiles to a chiral bicyclic dehydroalanine (Dha) are described. Of particular importance, radical carbon photolysis by a catalytic photoredox process using a simple method with a metal-free photocatalyst provides exceptional yields and selectivities at room temperature. Moreover, these 1,4-conjugate additions offer an excellent starting point for synthesizing enantiomerically pure carbon-β-substituted unnatural α-amino acids (UAAs), which could have a high potential for applications in chemical biology. American Chemical Society 2022-09-30 2022-11-04 /pmc/articles/PMC9639051/ /pubmed/36179039 http://dx.doi.org/10.1021/acs.joc.2c01774 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Oroz, Paula
Navo, Claudio D.
Avenoza, Alberto
Busto, Jesús H.
Corzana, Francisco
Jiménez-Osés, Gonzalo
Peregrina, Jesús M.
Towards Enantiomerically Pure Unnatural α-Amino Acids via Photoredox Catalytic 1,4-Additions to a Chiral Dehydroalanine
title Towards Enantiomerically Pure Unnatural α-Amino Acids via Photoredox Catalytic 1,4-Additions to a Chiral Dehydroalanine
title_full Towards Enantiomerically Pure Unnatural α-Amino Acids via Photoredox Catalytic 1,4-Additions to a Chiral Dehydroalanine
title_fullStr Towards Enantiomerically Pure Unnatural α-Amino Acids via Photoredox Catalytic 1,4-Additions to a Chiral Dehydroalanine
title_full_unstemmed Towards Enantiomerically Pure Unnatural α-Amino Acids via Photoredox Catalytic 1,4-Additions to a Chiral Dehydroalanine
title_short Towards Enantiomerically Pure Unnatural α-Amino Acids via Photoredox Catalytic 1,4-Additions to a Chiral Dehydroalanine
title_sort towards enantiomerically pure unnatural α-amino acids via photoredox catalytic 1,4-additions to a chiral dehydroalanine
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9639051/
https://www.ncbi.nlm.nih.gov/pubmed/36179039
http://dx.doi.org/10.1021/acs.joc.2c01774
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