Journal article
Sarah L Hejnosz, Danielle R. Beres, Alexander H Cocolas, M. Neal, Benjamin S Musiak, Marianne M B Hanna, A. Bloomfield, Thomas D. Montgomery
Organic Letters, 2023
Organic Letters, 2023
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APA
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Hejnosz, S. L., Beres, D. R., Cocolas, A. H., Neal, M., Musiak, B. S., Hanna, M. M. B., … Montgomery, T. D. (2023). [3 + 2] Cycloadditions of Tertiary Amine N-Oxides and Silyl Imines as an Innovative Route to 1,2-Diamines. Organic Letters.
Chicago/Turabian
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Hejnosz, Sarah L, Danielle R. Beres, Alexander H Cocolas, M. Neal, Benjamin S Musiak, Marianne M B Hanna, A. Bloomfield, and Thomas D. Montgomery. “[3 + 2] Cycloadditions of Tertiary Amine N-Oxides and Silyl Imines as an Innovative Route to 1,2-Diamines.” Organic Letters (2023).
MLA
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Hejnosz, Sarah L., et al. “[3 + 2] Cycloadditions of Tertiary Amine N-Oxides and Silyl Imines as an Innovative Route to 1,2-Diamines.” Organic Letters, 2023.
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@article{sarah2023a,
title = {[3 + 2] Cycloadditions of Tertiary Amine N-Oxides and Silyl Imines as an Innovative Route to 1,2-Diamines},
year = {2023},
journal = {Organic Letters},
author = {Hejnosz, Sarah L and Beres, Danielle R. and Cocolas, Alexander H and Neal, M. and Musiak, Benjamin S and Hanna, Marianne M B and Bloomfield, A. and Montgomery, Thomas D.}
}
Abstract
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.