Literature DB >> 29570926

Formation of Aminocyclopentadienes from Silyldihydropyridines: Ring Contractions Driven by Anion Stabilization.

Morgan M Walker1, Shuming Chen2, Brandon Q Mercado1, K N Houk2, Jonathan A Ellman1.   

Abstract

Highly functionalized aminocyclopentadienes can be formed through the rearrangement of anions generated from readily prepared 6-silyl-1,2-dihydropyridines by desilylation with fluoride. The scope and generality of the reaction was defined, and diverse transformations were performed on the highly functionalized products. A mechanism and driving force for the rearrangement were identified from experiments and DFT calculations.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  amines; density functional calculations; reaction mechanisms; rearrangement; ring contraction

Mesh：

Substances：

Year:  2018        PMID： 29570926      PMCID： PMC6040663          DOI： 10.1002/anie.201800596

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  17 in total

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9.  Unstabilized azomethine ylides for the stereoselective synthesis of substituted piperidines, tropanes, and azabicyclo[3.1.0] systems.

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  1 in total

Review 1.  Rhodium-Catalyzed C-H Alkenylation/Electrocyclization Cascade Provides Dihydropyridines That Serve as Versatile Intermediates to Diverse Nitrogen Heterocycles.

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Journal:  Acc Chem Res       Date:  2021-03-19       Impact factor: 22.384
  1 in total

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