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Angew Chem Int Ed Engl. 2018 May 28;57(22):6605-6609. doi: 10.1002/anie.201800596. Epub 2018 Apr 26.

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

Author information

1
Department of Chemistry, Yale University, 225 Prospect St., New Haven, CT, 06520, USA.
2
Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA, 90095-1569, USA.

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.

KEYWORDS:

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

PMID:
29570926
PMCID:
PMC6040663
DOI:
10.1002/anie.201800596
[Indexed for MEDLINE]
Free PMC Article

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