Journal of Organic Chemistry p. 12509 - 12525 (2015)
Update date:2022-08-11
Topics:
Bosset, Cyril
Angibaud, Patrick
Stanfield, Ian
Meerpoel, Lieven
Berthelot, Didier
Guérinot, Amandine
Cossy, Janine
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.
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