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Iron-Catalyzed Enantioselective Intramolecular Inverse Electron-Demand Hetero Diels–Alder Reactions: An Access to Bicyclic Dihydropyran Derivatives
Journal article   Open access   Peer reviewed

Iron-Catalyzed Enantioselective Intramolecular Inverse Electron-Demand Hetero Diels–Alder Reactions: An Access to Bicyclic Dihydropyran Derivatives

Jimmy Lauberteaux, Aurélien Lebrun, Arie van Der Lee, Marc Mauduit, Renata Marcia de Figueiredo and Jean-Marc Campagne
Organic Letters, Vol.21(24), pp.10007-10012
05/12/2019
PMID: 31825229

Abstract

Hetero Diels-Alder Iron catalysis Enantioselective catalysis
A highly enantioselective iron-catalyzed Intramolecular Inverse Electron-Demand Hetero Diels-Alder (IIEDHDA) reaction is reported. By using a chiral semicorrin ligand in the presence of 2,6 lutidine, good isolated yields and excellent enantioselectivities were observed (up to 96% ee). Thanks to the versatile post-functionalization of the acyl-imidazole moiety, this methodology represents a unique example of the straightforward construction of highly valuable enantioenriched bicyclic dihydropyran derivatives.
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