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

DOI

10.1021/acs.orglett.4c02013

Authors

Alexander H. Cocolas, Duquesne University
Aiden M. Lane, Duquesne University
Benjamin S. Musiak, Duquesne University
Eric J. Chartier, Duquesne University
Derek A. Bedillion, Duquesne University
Sarah L. Hejnosz, Duquesne University
Jeffrey J. Rohde, Franciscan University of Steubenville
Paul A. Lummis, Duquesne University
Jeffrey D. Evanseck, Duquesne University
Thomas D. Montgomery, Duquesne University

Document Type

Journal Article

Publication Date

8-9-2024

Publication Title

Organic Letters

Volume

26

Issue

31

First Page

6546

Last Page

6550

ISSN

15237060

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.

Open Access

Hybrid_Gold

Repository Citation

Cocolas, A., Lane, A., Musiak, B., Chartier, E., Bedillion, D., Hejnosz, S., Rohde, J., Lummis, P., Evanseck, J., & Montgomery, T. (2024). Diastereoselective [3 + 2] Cycloaddition between Tertiary Amine N-Oxides and Substituted Alkenes to Access 7-Azanorbornanes. Organic Letters, 26 (31), 6546-6550. https://doi.org/10.1021/acs.orglett.4c02013