Aziridine Opening via a Phenonium Ion Enables Synthesis of Complex Phenethylamine Derivatives

Hannah Holst, Jack T. Floreancig, Casey B Ritts, Nicholas J. Race

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

We report that the treatment of unsymmetrical 2,3-disubstituted aziridines with TiCl4 yields β-phenethylamine products via the intermediacy of a phenonium ion. Derivatization of the products obtained via this method is demonstrated. Computational analysis of the reaction pathway provides insight into the reaction mechanism, including the selectivity of the phenonium opening.

Original languageEnglish (US)
Pages (from-to)501-505
Number of pages5
JournalOrganic Letters
Volume24
Issue number2
DOIs
StatePublished - Jan 21 2022

Bibliographical note

Funding Information:
Dr. Shiyan Xu (UMN) is acknowledged for preliminary experiments on the project. Kathryn Rynders (UMN) and Dr. Victor G. Young, Jr. (UMN) are acknowledged for X-ray crystallographic analysis of 6b . Professor Jolene Reid (UBC) and Dr. Juanvi Alegre Requena (CSU) are acknowledged for assistance with computational calculations and analysis. This work was funded by the National Institute of General Medical Sciences of the National Institutes of Health under award number R35GM137920. We also acknowledge the NIH Shared Instrumentation Grant S10OD011952.

Publisher Copyright:
© 2021 American Chemical Society.

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