title: Investigation of the Diels-Alder cycloadditions of 2(H)-1,4-oxazin-2-ones.
abstract: [Reaction: see text]. A variety of 5-chloro-2(H)-1,4-oxazin-2-ones bearing a range of substituents at their 3- and 6-positions undergo Diels-Alder cycloaddition as a 2-azadiene component with electron-rich, electron-deficient, and electron-neutral dienophiles. These reactions proceed with moderate regio- and stereoselectivity to afford relatively stable and readily isolable bridged bicyclic lactone cycloadducts. Chemical manipulation of these cycloadducts affords highly substituted and functionally rich piperidines. The regio- and stereochemical preferences of the cycloadditions of 5-chloro-2(H)-1,4-oxazin-2-ones are investigated computationally using density functional theory (B3LYP/6-31G).
authors.affiliation: Department of Chemistry, King's College, Strand, London WC2R 2LS, UK. kamyar.afarinkia@kcl.ac.uk
authors.forename: Kamyar
authors.initials: K
authors.lastname: Afarinkia
authors.forename: Akmal
authors.initials: A
authors.lastname: Bahar
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Bearpark
authors.forename: Yésica
authors.initials: Y
authors.lastname: Garcia-Ramos
authors.forename: Andrea
authors.initials: A
authors.lastname: Ruggiero
authors.forename: Judi
authors.initials: J
authors.lastname: Neuss
authors.forename: Maushami
authors.initials: M
authors.lastname: Vyas