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Formation of Aminocyclopentadienes from Silyldihydropyridines: Ring Contractions Driven by Anion Stabilization
Author(s) -
Walker Morgan M.,
Chen Shuming,
Mercado Brandon Q.,
Houk K. N.,
Ellman Jonathan A.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201800596
Subject(s) - fluoride , silylation , chemistry , generality , ion , ring (chemistry) , scope (computer science) , combinatorial chemistry , reaction mechanism , mechanism (biology) , computational chemistry , organic chemistry , inorganic chemistry , catalysis , computer science , psychology , philosophy , epistemology , psychotherapist , programming language
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.