title: Iron-Catalyzed Synthesis of C2 Aryl- and N-Heteroaryl-Substituted Tetrahydropyrans.
abstract: 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.
authors.affiliation: Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI)-UMR 8231, ESPCI ParisTech , CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
authors.forename: Cyril
authors.initials: C
authors.lastname: Bosset
authors.affiliation: Janssen Research & Development , Oncology Medicinal Chemistry, Campus de Maigremont-BP615-27106, Val de Reuil Cedex, France.
authors.forename: Patrick
authors.initials: P
authors.lastname: Angibaud
authors.affiliation: Janssen Research & Development , Oncology Medicinal Chemistry, Campus de Maigremont-BP615-27106, Val de Reuil Cedex, France.
authors.forename: Ian
authors.initials: I
authors.lastname: Stanfield
authors.affiliation: Janssen Research & Development , Janssen Pharmaceutica N.V., Turnhoutsweg 30, 2340 Beerse, Belgium.
authors.forename: Lieven
authors.initials: L
authors.lastname: Meerpoel
authors.affiliation: Janssen Research & Development , Oncology Medicinal Chemistry, Campus de Maigremont-BP615-27106, Val de Reuil Cedex, France.
authors.forename: Didier
authors.initials: D
authors.lastname: Berthelot
authors.affiliation: Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI)-UMR 8231, ESPCI ParisTech , CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
authors.forename: Amandine
authors.initials: A
authors.lastname: Guérinot
authors.affiliation: Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI)-UMR 8231, ESPCI ParisTech , CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
authors.forename: Janine
authors.initials: J
authors.lastname: Cossy