Synthesis of Macroheterocycles through Intramolecular Oxidative Coupling of Furanoid β-Ketoesters

It's all in the CAN: Cerium ammonium nitrate (CAN) promotes the oxidative radical cyclization of furan β‐ketoesters to form macrocycles of varying ring sizes. The reaction is tolerant of unsaturation, oxygenation, and nitrogen and oxygen heterocycles in the carbon backbone tether.

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2012-05, Vol.51 (19), p.4726-4730
Main Authors: Nicolaou, K. C., Hale, Christopher R. H., Ebner, Christian, Nilewski, Christian, Ahles, Christopher F., Rhoades, Derek
Format: Article
Language:English
Subjects:
Acetals - chemical synthesis
Acetals - chemistry
Catalysis
Cerium - chemistry
cerium ammonium nitrate
Cyclization
Esters
Free Radicals - chemistry
furanocembranoids
Furans - chemistry
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
macrocyclization
Nitrates - chemistry
Oxidation-Reduction
radical reactions
synthetic methods
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Description
Summary:It's all in the CAN: Cerium ammonium nitrate (CAN) promotes the oxidative radical cyclization of furan β‐ketoesters to form macrocycles of varying ring sizes. The reaction is tolerant of unsaturation, oxygenation, and nitrogen and oxygen heterocycles in the carbon backbone tether.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201201538