Diastereoselective [3 + 2] Cycloaddition between Tertiary Amine N-Oxides and Substituted Alkenes to Access 7-Azanorbornanes


Journal article


Alexander H Cocolas, Aiden M Lane, Benjamin S Musiak, Eric J. Chartier, Derek A Bedillion, Sarah L Hejnosz, P. Lummis, J. Evanseck, Thomas D. Montgomery
Organic Letters, 2024

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APA   Click to copy
Cocolas, A. H., Lane, A. M., Musiak, B. S., Chartier, E. J., Bedillion, D. A., Hejnosz, S. L., … Montgomery, T. D. (2024). Diastereoselective [3 + 2] Cycloaddition between Tertiary Amine N-Oxides and Substituted Alkenes to Access 7-Azanorbornanes. Organic Letters.


Chicago/Turabian   Click to copy
Cocolas, Alexander H, Aiden M Lane, Benjamin S Musiak, Eric J. Chartier, Derek A Bedillion, Sarah L Hejnosz, P. Lummis, J. Evanseck, and Thomas D. Montgomery. “Diastereoselective [3 + 2] Cycloaddition between Tertiary Amine N-Oxides and Substituted Alkenes to Access 7-Azanorbornanes.” Organic Letters (2024).


MLA   Click to copy
Cocolas, Alexander H., et al. “Diastereoselective [3 + 2] Cycloaddition between Tertiary Amine N-Oxides and Substituted Alkenes to Access 7-Azanorbornanes.” Organic Letters, 2024.


BibTeX   Click to copy

@article{alexander2024a,
  title = {Diastereoselective [3 + 2] Cycloaddition between Tertiary Amine N-Oxides and Substituted Alkenes to Access 7-Azanorbornanes},
  year = {2024},
  journal = {Organic Letters},
  author = {Cocolas, Alexander H and Lane, Aiden M and Musiak, Benjamin S and Chartier, Eric J. and Bedillion, Derek A and Hejnosz, Sarah L and Lummis, P. and Evanseck, J. and Montgomery, Thomas D.}
}

Abstract

We have developed a diastereoselective synthesis of 43 novel 7-azanorbornanes using tertiary amine N-oxides and substituted alkenes. Our method uses an efficient [3 + 2] cycloaddition, starting from either commercially available or easily accessible precursors to generate yields up to 97% and diastereomeric ratios up to >20:1. Density functional theory (DFT) calculations were performed, suggesting that the observed diastereoselectivity is likely due to steric considerations.


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