Radical Functionalization of Unsaturated Amino Acids: Synthesis of Side-Chain-Fluorinated, Azido-Substituted, and Hydroxylated Amino Acids

[Image: see text] A range of enantiomerically pure protected side-chain-fluorinated amino acids has been prepared (13 examples) by treatment of protected amino acids containing unsaturated side chains with a combination of Fe(III)/NaBH(4) and Selectfluor. The modification of the conditions by replac...

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Autores principales: Reeve, Philip A. P., Grabowska, Urszula, Oden, Lourdes Salvador, Wiktelius, Daniel, Wångsell, Fredrik, Jackson, Richard F. W.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648964/
https://www.ncbi.nlm.nih.gov/pubmed/31460183
http://dx.doi.org/10.1021/acsomega.9b01509
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author Reeve, Philip A. P.
Grabowska, Urszula
Oden, Lourdes Salvador
Wiktelius, Daniel
Wångsell, Fredrik
Jackson, Richard F. W.
author_facet Reeve, Philip A. P.
Grabowska, Urszula
Oden, Lourdes Salvador
Wiktelius, Daniel
Wångsell, Fredrik
Jackson, Richard F. W.
author_sort Reeve, Philip A. P.
collection PubMed
description [Image: see text] A range of enantiomerically pure protected side-chain-fluorinated amino acids has been prepared (13 examples) by treatment of protected amino acids containing unsaturated side chains with a combination of Fe(III)/NaBH(4) and Selectfluor. The modification of the conditions by replacement of Selectfluor with NaN(3) allowed the preparation of side-chain azido-substituted amino acids (five examples), which upon catalytic hydrogenation gave the corresponding amines, isolated as lactams (four examples). Radical hydration of the unsaturated side chains leading to side-chain-hydroxylated protected amino acids has also been demonstrated.
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spelling pubmed-66489642019-08-27 Radical Functionalization of Unsaturated Amino Acids: Synthesis of Side-Chain-Fluorinated, Azido-Substituted, and Hydroxylated Amino Acids Reeve, Philip A. P. Grabowska, Urszula Oden, Lourdes Salvador Wiktelius, Daniel Wångsell, Fredrik Jackson, Richard F. W. ACS Omega [Image: see text] A range of enantiomerically pure protected side-chain-fluorinated amino acids has been prepared (13 examples) by treatment of protected amino acids containing unsaturated side chains with a combination of Fe(III)/NaBH(4) and Selectfluor. The modification of the conditions by replacement of Selectfluor with NaN(3) allowed the preparation of side-chain azido-substituted amino acids (five examples), which upon catalytic hydrogenation gave the corresponding amines, isolated as lactams (four examples). Radical hydration of the unsaturated side chains leading to side-chain-hydroxylated protected amino acids has also been demonstrated. American Chemical Society 2019-06-21 /pmc/articles/PMC6648964/ /pubmed/31460183 http://dx.doi.org/10.1021/acsomega.9b01509 Text en Copyright © 2019 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Reeve, Philip A. P.
Grabowska, Urszula
Oden, Lourdes Salvador
Wiktelius, Daniel
Wångsell, Fredrik
Jackson, Richard F. W.
Radical Functionalization of Unsaturated Amino Acids: Synthesis of Side-Chain-Fluorinated, Azido-Substituted, and Hydroxylated Amino Acids
title Radical Functionalization of Unsaturated Amino Acids: Synthesis of Side-Chain-Fluorinated, Azido-Substituted, and Hydroxylated Amino Acids
title_full Radical Functionalization of Unsaturated Amino Acids: Synthesis of Side-Chain-Fluorinated, Azido-Substituted, and Hydroxylated Amino Acids
title_fullStr Radical Functionalization of Unsaturated Amino Acids: Synthesis of Side-Chain-Fluorinated, Azido-Substituted, and Hydroxylated Amino Acids
title_full_unstemmed Radical Functionalization of Unsaturated Amino Acids: Synthesis of Side-Chain-Fluorinated, Azido-Substituted, and Hydroxylated Amino Acids
title_short Radical Functionalization of Unsaturated Amino Acids: Synthesis of Side-Chain-Fluorinated, Azido-Substituted, and Hydroxylated Amino Acids
title_sort radical functionalization of unsaturated amino acids: synthesis of side-chain-fluorinated, azido-substituted, and hydroxylated amino acids
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648964/
https://www.ncbi.nlm.nih.gov/pubmed/31460183
http://dx.doi.org/10.1021/acsomega.9b01509
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