Cargando…
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...
Autores principales: | , , , |
---|---|
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 |
_version_ | 1782441253442420736 |
---|---|
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. |
format | Online Article Text |
id | pubmed-4933940 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | American
Chemical Society |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT punkmolly palladiumcatalyzedenantioselectiveheinereaction AT merkleycharlotte palladiumcatalyzedenantioselectiveheinereaction AT kennedykatlyn palladiumcatalyzedenantioselectiveheinereaction AT morganjeremyb palladiumcatalyzedenantioselectiveheinereaction |