Highly functionalized aminocyclopentadienes can be formed through the rearrangement of anions generated from readily prepared silyldihydropyridines 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.

Formation of aminocyclopentadienes from silyldihydropyridines: Ring contractions driven by anion stabilization

2019 Spring National Meeting

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