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Iron-Catalyzed Synthesis of C2 Aryl- and N‑Heteroaryl-Substituted Tetrahydropyrans

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journal contribution
posted on 18.12.2015, 00:00 authored by Cyril Bosset, Patrick Angibaud, Ian Stanfield, Lieven Meerpoel, Didier Berthelot, Amandine Guérinot, Janine Cossy
An iron-catalyzed cyclization of hydroxy allylic derivatives into tetrahydropyrans possessing an N-heteroaryl at C2 is disclosed. The reaction proceeds with good yield and in high diastereoselectivity in favor of the more stable isomer. The diastereoselectivity results from an iron-induced reopening of the tetrahydropyrans, allowing a thermodynamic equilibration. The method allows access to a variety of 2,6-disubstituted as well as 2,4,6-trisubstituted tetrahydropyrans that could be considered as attractive scaffolds for the pharmaceutical industry.