Literature DB >> 34967220

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

Hannah M Holst1, Jack T Floreancig1, Casey B Ritts1, Nicholas J Race1.   

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.

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Year:  2021        PMID： 34967220      PMCID： PMC8796817          DOI： 10.1021/acs.orglett.1c03857

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  7 in total

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Authors:  K W Bentley
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2.  Reagent Control Enables Selective and Regiodivergent Opening of Unsymmetrical Phenonium Ions.

Authors:  Shiyan Xu; Hannah M Holst; Shelby B McGuire; Nicholas J Race
Journal:  J Am Chem Soc       Date:  2020-04-24       Impact factor: 15.419

3.  Asymmetric Copper-Catalyzed Intermolecular Aminoarylation of Styrenes: Efficient Access to Optical 2,2-Diarylethylamines.

Authors:  Dinghai Wang; Lianqian Wu; Fei Wang; Xiaolong Wan; Pinhong Chen; Zhenyang Lin; Guosheng Liu
Journal:  J Am Chem Soc       Date:  2017-05-10       Impact factor: 15.419

4.  Highly stereoselective 7-endo-trig/ring contraction cascade to construct pyrrolo[1,2-a]quinoline derivatives.

Authors:  Xinyu Li; Cheng Li; Wenjing Zhang; Xiang Lu; Shiqing Han; Ran Hong
Journal:  Org Lett       Date:  2010-04-16       Impact factor: 6.005

5.  Fused piperidines as a novel class of potent and orally available transient receptor potential melastatin type 8 (TRPM8) antagonists.

Authors:  Nuria A Tamayo; Yunxin Bo; Vijay Gore; Vu Ma; Nobuko Nishimura; Phi Tang; Hong Deng; Lana Klionsky; Sonya G Lehto; Weiya Wang; Brad Youngblood; Jiyun Chen; Tiffany L Correll; Michael D Bartberger; Narender R Gavva; Mark H Norman
Journal:  J Med Chem       Date:  2012-02-13       Impact factor: 7.446

6.  Escape from flatland: increasing saturation as an approach to improving clinical success.

Authors:  Frank Lovering; Jack Bikker; Christine Humblet
Journal:  J Med Chem       Date:  2009-11-12       Impact factor: 7.446

Review 7.  Aziridines: epoxides' ugly cousins?

Authors:  J B Sweeney
Journal:  Chem Soc Rev       Date:  2002-09       Impact factor: 54.564
  7 in total

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