title: Stereoselective Synthesis of Substituted Tetrahydropyrans and Isochromans by Cyclization of Phenylseleno Alcohols.
abstract: A selenium-mediated strategy for the stereoselective synthesis of substituted tetrahydropyrans and isochromans has been developed starting from δ-phenylseleno ketones. After enantioselective reduction, the chiral nonracemic phenylseleno alcohols were oxidized to the corresponding selenones, which underwent an effcient 6-exo-tet ring-closure reaction.
authors.affiliation: †Dipartimento di Scienze Farmaceutiche, Università di Perugia, Via del Liceo 1, 06123 Perugia, Italy.
authors.forename: Andrea
authors.initials: A
authors.lastname: Temperini
authors.affiliation: ‡Dipartimento di Scienze Chimiche, Università di Messina, Viale F. Stagno d'Alcontres 31, 98166 Messina, Italy.
authors.forename: Anna
authors.initials: A
authors.lastname: Barattucci
authors.affiliation: ‡Dipartimento di Scienze Chimiche, Università di Messina, Viale F. Stagno d'Alcontres 31, 98166 Messina, Italy.
authors.forename: Paola Maria
authors.initials: PM
authors.lastname: Bonaccorsi
authors.affiliation: †Dipartimento di Scienze Farmaceutiche, Università di Perugia, Via del Liceo 1, 06123 Perugia, Italy.
authors.forename: Ornelio
authors.initials: O
authors.lastname: Rosati
authors.affiliation: §Dipartimento di Chimica, Biologia e Biotecnologie, Università di Perugia, Via Elce di Sotto 8, 06123 Perugia, Italy.
authors.forename: Lucio
authors.initials: L
authors.lastname: Minuti
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D002839:Chromans / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D002839:Chromans; D016566:Organoselenium Compounds; D011714:Pyrans