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[3 + 2] Cycloadditions of Tertiary Amine N-Oxides and Silyl Imines as an Innovative Route to 1,2-Diamines
[Image: see text] We have developed a one-pot synthetic method for producing 1,2-diamines from easily prepared and commercially available precursors through a formal umpolung process. Our method utilizes an efficient [3 + 2] cycloaddition as the key step in forming substituted 1,2-diamines in modera...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2023
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10325142/ https://www.ncbi.nlm.nih.gov/pubmed/37318514 http://dx.doi.org/10.1021/acs.orglett.3c01396 |
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author | Hejnosz, Sarah L. Beres, Danielle R. Cocolas, Alexander H. Neal, Martin J. Musiak, Benjamin S. Hanna, Marianne M. B. Bloomfield, Aaron J. Montgomery, Thomas D. |
author_facet | Hejnosz, Sarah L. Beres, Danielle R. Cocolas, Alexander H. Neal, Martin J. Musiak, Benjamin S. Hanna, Marianne M. B. Bloomfield, Aaron J. Montgomery, Thomas D. |
author_sort | Hejnosz, Sarah L. |
collection | PubMed |
description | [Image: see text] We have developed a one-pot synthetic method for producing 1,2-diamines from easily prepared and commercially available precursors through a formal umpolung process. Our method utilizes an efficient [3 + 2] cycloaddition as the key step in forming substituted 1,2-diamines in moderate to high yields. These resulting compounds can undergo subsequent transformations, demonstrating their utility as synthetic building blocks for more complex scaffolds. Finally, we propose a reasonable mechanism for this transformation using density functional theory modeling, justifying the experimental observations. |
format | Online Article Text |
id | pubmed-10325142 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-103251422023-07-07 [3 + 2] Cycloadditions of Tertiary Amine N-Oxides and Silyl Imines as an Innovative Route to 1,2-Diamines Hejnosz, Sarah L. Beres, Danielle R. Cocolas, Alexander H. Neal, Martin J. Musiak, Benjamin S. Hanna, Marianne M. B. Bloomfield, Aaron J. Montgomery, Thomas D. Org Lett [Image: see text] We have developed a one-pot synthetic method for producing 1,2-diamines from easily prepared and commercially available precursors through a formal umpolung process. Our method utilizes an efficient [3 + 2] cycloaddition as the key step in forming substituted 1,2-diamines in moderate to high yields. These resulting compounds can undergo subsequent transformations, demonstrating their utility as synthetic building blocks for more complex scaffolds. Finally, we propose a reasonable mechanism for this transformation using density functional theory modeling, justifying the experimental observations. American Chemical Society 2023-06-15 /pmc/articles/PMC10325142/ /pubmed/37318514 http://dx.doi.org/10.1021/acs.orglett.3c01396 Text en © 2023 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 | Hejnosz, Sarah L. Beres, Danielle R. Cocolas, Alexander H. Neal, Martin J. Musiak, Benjamin S. Hanna, Marianne M. B. Bloomfield, Aaron J. Montgomery, Thomas D. [3 + 2] Cycloadditions of Tertiary Amine N-Oxides and Silyl Imines as an Innovative Route to 1,2-Diamines |
title | [3 + 2] Cycloadditions
of Tertiary Amine N-Oxides and Silyl Imines
as an Innovative Route to 1,2-Diamines |
title_full | [3 + 2] Cycloadditions
of Tertiary Amine N-Oxides and Silyl Imines
as an Innovative Route to 1,2-Diamines |
title_fullStr | [3 + 2] Cycloadditions
of Tertiary Amine N-Oxides and Silyl Imines
as an Innovative Route to 1,2-Diamines |
title_full_unstemmed | [3 + 2] Cycloadditions
of Tertiary Amine N-Oxides and Silyl Imines
as an Innovative Route to 1,2-Diamines |
title_short | [3 + 2] Cycloadditions
of Tertiary Amine N-Oxides and Silyl Imines
as an Innovative Route to 1,2-Diamines |
title_sort | [3 + 2] cycloadditions
of tertiary amine n-oxides and silyl imines
as an innovative route to 1,2-diamines |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10325142/ https://www.ncbi.nlm.nih.gov/pubmed/37318514 http://dx.doi.org/10.1021/acs.orglett.3c01396 |
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