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Palladium-Catalyzed, Enantioselective Heine Reaction

[Image: see text] Aziridines are important synthetic intermediates for the generation of nitrogen-containing molecules. N-Acylaziridines undergo rearrangement by ring expansion to produce oxazolines, a process known as the Heine reaction. The first catalytic, enantioselective Heine reaction is repor...

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Autores principales: Punk, Molly, Merkley, Charlotte, Kennedy, Katlyn, Morgan, Jeremy B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2016
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4933940/
https://www.ncbi.nlm.nih.gov/pubmed/27398262
http://dx.doi.org/10.1021/acscatal.6b01400
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author Punk, Molly
Merkley, Charlotte
Kennedy, Katlyn
Morgan, Jeremy B.
author_facet Punk, Molly
Merkley, Charlotte
Kennedy, Katlyn
Morgan, Jeremy B.
author_sort Punk, Molly
collection PubMed
description [Image: see text] Aziridines are important synthetic intermediates for the generation of nitrogen-containing molecules. N-Acylaziridines undergo rearrangement by ring expansion to produce oxazolines, a process known as the Heine reaction. The first catalytic, enantioselective Heine reaction is reported for meso-N-acylaziridines where a palladium(II)–diphosphine complex is employed. The highly enantioenriched oxazoline products are valuable organic synthons and potential ligands for transition-metal catalysis.
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spelling pubmed-49339402016-07-07 Palladium-Catalyzed, Enantioselective Heine Reaction Punk, Molly Merkley, Charlotte Kennedy, Katlyn Morgan, Jeremy B. ACS Catal [Image: see text] Aziridines are important synthetic intermediates for the generation of nitrogen-containing molecules. N-Acylaziridines undergo rearrangement by ring expansion to produce oxazolines, a process known as the Heine reaction. The first catalytic, enantioselective Heine reaction is reported for meso-N-acylaziridines where a palladium(II)–diphosphine complex is employed. The highly enantioenriched oxazoline products are valuable organic synthons and potential ligands for transition-metal catalysis. American Chemical Society 2016-06-15 2016-07-01 /pmc/articles/PMC4933940/ /pubmed/27398262 http://dx.doi.org/10.1021/acscatal.6b01400 Text en Copyright © 2016 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Punk, Molly
Merkley, Charlotte
Kennedy, Katlyn
Morgan, Jeremy B.
Palladium-Catalyzed, Enantioselective Heine Reaction
title Palladium-Catalyzed, Enantioselective Heine Reaction
title_full Palladium-Catalyzed, Enantioselective Heine Reaction
title_fullStr Palladium-Catalyzed, Enantioselective Heine Reaction
title_full_unstemmed Palladium-Catalyzed, Enantioselective Heine Reaction
title_short Palladium-Catalyzed, Enantioselective Heine Reaction
title_sort palladium-catalyzed, enantioselective heine reaction
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4933940/
https://www.ncbi.nlm.nih.gov/pubmed/27398262
http://dx.doi.org/10.1021/acscatal.6b01400
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AT morganjeremyb palladiumcatalyzedenantioselectiveheinereaction