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

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.

SUBMITTER: Walker MM

PROVIDER: S-EPMC6040663 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature

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

Walker Morgan M MM Chen Shuming S Mercado Brandon Q BQ Houk K N KN Ellman Jonathan A JA

Angewandte Chemie (International ed. in English) 20180426 22

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. ...[more]

PMID: 29570926

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