Photoredox α-Vinylation of α-Amino Acids and N-Aryl Amines

[Image: see text] A new coupling protocol has been developed that allows the union of vinyl sulfones with photoredox-generated α-amino radicals to provide allylic amines of broad diversity. Direct C–H vinylations of N-aryl tertiary amines, as well as decarboxylative vinylations of N-Boc α-amino acid...

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Autores principales: Noble, Adam, MacMillan, David W. C.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4140496/
https://www.ncbi.nlm.nih.gov/pubmed/25026314
http://dx.doi.org/10.1021/ja506094d
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author Noble, Adam
MacMillan, David W. C.
author_facet Noble, Adam
MacMillan, David W. C.
author_sort Noble, Adam
collection PubMed
description [Image: see text] A new coupling protocol has been developed that allows the union of vinyl sulfones with photoredox-generated α-amino radicals to provide allylic amines of broad diversity. Direct C–H vinylations of N-aryl tertiary amines, as well as decarboxylative vinylations of N-Boc α-amino acids, proceed in high yield and with excellent olefin geometry control. The utility of this new allyl amine forming reaction has been demonstrated via the syntheses of several natural products and a number of established pharmacophores.
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spelling pubmed-41404962015-07-14 Photoredox α-Vinylation of α-Amino Acids and N-Aryl Amines Noble, Adam MacMillan, David W. C. J Am Chem Soc [Image: see text] A new coupling protocol has been developed that allows the union of vinyl sulfones with photoredox-generated α-amino radicals to provide allylic amines of broad diversity. Direct C–H vinylations of N-aryl tertiary amines, as well as decarboxylative vinylations of N-Boc α-amino acids, proceed in high yield and with excellent olefin geometry control. The utility of this new allyl amine forming reaction has been demonstrated via the syntheses of several natural products and a number of established pharmacophores. American Chemical Society 2014-07-14 2014-08-20 /pmc/articles/PMC4140496/ /pubmed/25026314 http://dx.doi.org/10.1021/ja506094d Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Noble, Adam
MacMillan, David W. C.
Photoredox α-Vinylation of α-Amino Acids and N-Aryl Amines
title Photoredox α-Vinylation of α-Amino Acids and N-Aryl Amines
title_full Photoredox α-Vinylation of α-Amino Acids and N-Aryl Amines
title_fullStr Photoredox α-Vinylation of α-Amino Acids and N-Aryl Amines
title_full_unstemmed Photoredox α-Vinylation of α-Amino Acids and N-Aryl Amines
title_short Photoredox α-Vinylation of α-Amino Acids and N-Aryl Amines
title_sort photoredox α-vinylation of α-amino acids and n-aryl amines
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4140496/
https://www.ncbi.nlm.nih.gov/pubmed/25026314
http://dx.doi.org/10.1021/ja506094d
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AT macmillandavidwc photoredoxavinylationofaaminoacidsandnarylamines

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