A Pd‐Catalyzed Annulation Strategy to Linearly Fused Functionalized N‐Heterocycles

Linearly fused polycyclic piperidines represent common substructures in natural products and biologically active small molecules. We have devised a Pd‐catalyzed annulation strategy to these compounds that converts readily available 2‐tetralones and indanones into these scaffolds with the potential f...

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Bibliographic Details
Published in:Chemistry : a European journal 2024-04, Vol.30 (21), p.e202400116-n/a
Main Authors: Hoteite, Larry, Allen, Benjamin D. W., Elhajj, Ms. Ergaiya A., Meijer, Anthony J. H. M., Harrity, Joseph P. A.
Format: Article
Language:English
Subjects:
allylic alkylation
Biological activity
catalysis
Chemical reactions
diastereoselective
enantioselective
Natural products
Organic chemistry
piperidine
Stereoselectivity
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Summary:Linearly fused polycyclic piperidines represent common substructures in natural products and biologically active small molecules. We have devised a Pd‐catalyzed annulation strategy to these compounds that converts readily available 2‐tetralones and indanones into these scaffolds with the potential for control of both enantio‐ and diastereoselectivity. Importantly, these compounds can be chemoselectively functionalized, providing an efficient and robust methodology to these important nitrogen‐containing molecules. We report a stereoselective Pd‐catalyzed annulation strategy to linearly fused polycyclic piperidines from readily available substrates. These products can be chemoselectively functionalized to generate analogs that represent common substructures in bioactive compounds.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202400116