title: Controlled heterocyclization/cross-coupling domino reaction of β,γ-allendiols and α-allenic esters: method and mechanistic insight for the preparation of functionalized buta-1,3-dienyl dihydropyrans.
abstract: Starting from β,γ-allendiols and α-allenic acetates, a chemo- and regiocontrolled palladium-catalyzed methodology has provided access to enantiopure 3,6-dihydropyrans that bear a buta-1,3-dienyl moiety. Thus, it has been demonstrated for the first time that the preparation of six-membered heterocycles through cross-coupling reactions of two different allenes can be accomplished. These heterocyclization/cross-coupling reactions have been developed experimentally and their mechanisms have additionally been investigated by a computational study.
authors.affiliation: Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica I, Unidad Asociada al CSIC, Facultad de Química, Universidad Complutense de Madrid, 28040 Madrid (Spain), Fax: (+34) 91-3944103. alcaideb@quim.ucm.es.
authors.forename: Benito
authors.initials: B
authors.lastname: Alcaide
authors.forename: Pedro
authors.initials: P
authors.lastname: Almendros
authors.forename: Teresa
authors.initials: T
authors.lastname: Martínez del Campo
authors.forename: M Teresa
authors.initials: MT
authors.lastname: Quirós
authors.forename: Elena
authors.initials: E
authors.lastname: Soriano
authors.forename: José L
authors.initials: JL
authors.lastname: Marco-Contelles
mesh_terms: D003500:Cyclization; D004952:Esters; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D011789:Quantum Theory; D013237:Stereoisomerism
chemical_list: D004952:Esters; D006571:Heterocyclic Compounds; D011714:Pyrans; D010165:Palladium
keywords: allenes; density functional calculations; palladium; reaction mechanisms; regioselectivity