title: Preparation of α-imino aldehydes by [1,3]-rearrangements of O-alkenyl oximes.
abstract: The synthesis of α-imino aldehydes has been achieved through the thermal [1,3]-rearrangement of O-alkenyl benzophenone oximes. A copper-mediated C-O bond coupling between benzophenone oxime and alkenyl boronic acids provides facile access to the required O-alkenyl oximes and a Horner-Wadsworth-Emmons olefination can be applied to the α-imino aldehyde products to give γ-imino-α,β-unsaturated esters. The scope of the method is described and mechanistic experiments are discussed.
authors.affiliation: Department of Chemistry, University of Illinois at Chicago , 845 West Taylor Street, Chicago, Illinois 60607, United States.
authors.forename: Dimitra
authors.initials: D
authors.lastname: Kontokosta
authors.forename: Daniel S
authors.initials: DS
authors.lastname: Mueller
authors.forename: Heng-Yen
authors.initials: HY
authors.lastname: Wang
authors.forename: Laura L
authors.initials: LL
authors.lastname: Anderson