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

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.

SUBMITTER: Holst HM

PROVIDER: S-EPMC8796817 | biostudies-literature | 2022 Jan

REPOSITORIES: biostudies-literature

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

Holst Hannah M HM Floreancig Jack T JT Ritts Casey B CB Race Nicholas J NJ

Organic letters 20211230 2

We report that the treatment of unsymmetrical 2,3-disubstituted aziridines with TiCl<sub>4</sub> 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. ...[more]

PMID: 34967220

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