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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...

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Autores principales: 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.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
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.
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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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