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Synthesis of Macroheterocycles through Intramolecular Oxidative Coupling of Furanoid β‐Ketoesters
Author(s) -
Nicolaou K. C.,
Hale Christopher R. H.,
Ebner Christian,
Nilewski Christian,
Ahles Christopher F.,
Rhoades Derek
Publication year - 2012
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.201201538
Subject(s) - intramolecular force , chemistry , oxidative phosphorylation , degree of unsaturation , cerium , furan , oxidative coupling of methane , ring (chemistry) , ammonium nitrate , ceric ammonium nitrate , oxygen , medicinal chemistry , organic chemistry , catalysis , biochemistry , polymer , grafting
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.