Loading...
1,3-Allylic Strain as a Strategic Diversification Element For Constructing Libraries of Substituted 2-Arylpiperidines
Coombs, Thomas Lushington, Gerald H. Douglas, Justin T. Aubé, Jeffrey
Coombs, Thomas
Lushington, Gerald H.
Douglas, Justin T.
Aubé, Jeffrey
Citations
Altmetric:
Abstract
Flipping diversity—Minimization of 1,3-allylic strain is a recurring element in the design of a
stereochemically- and spatially-diverse collection of 2-arylpiperidines. Here, stereochemicallydiverse
scaffolding is first constructed using A1,3 strain to guide the regioselective addition of
nucleophiles, which serve as handles for further substitution. N-substitution with alkyl and acyl
substituents again leverages A1,3 strain to direct each stereoisomer to two different conformer
populations, doubling the number of library members
Description
Date
2011-03-14
Journal Title
Journal ISSN
Volume Title
Publisher
Wiley
Collections
Research Projects
Organizational Units
Journal Issue
Keywords
Arylpiperidines, 1, 3-allylic strain, Fürst–Plattner, Shape diversity, Conformational diversity
Citation
Coombs, T. C., Lushington, G. H., Douglas, J., & Aubé, J. (2011). 1,3-Allylic Strain as a Strategic Diversification Element For Constructing Libraries of Substituted 2-Arylpiperidines. Angewandte Chemie (International Ed. in English), 50(12), 2734–2737. http://doi.org/10.1002/anie.201007133