title: Catalyst-controlled Wacker-type oxidation: facile access to functionalized aldehydes.
abstract: The aldehyde-selective oxidation of alkenes bearing diverse oxygen groups in the allylic and homoallylic position was accomplished with a nitrite-modified Wacker oxidation. Readily available oxygenated alkenes were oxidized in up to 88% aldehyde yield and as high as 97% aldehyde selectivity. The aldehyde-selective oxidation enabled the rapid, enantioselective synthesis of an important pharmaceutical agent, atomoxetine. Finally, the influence of proximal functional groups on this anti-Markovnikov reaction was explored, providing important preliminary mechanistic insight.
authors.affiliation: Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.
authors.forename: Zachary K
authors.initials: ZK
authors.lastname: Wickens
authors.forename: Kacper
authors.initials: K
authors.lastname: Skakuj
authors.forename: Bill
authors.initials: B
authors.lastname: Morandi
authors.forename: Robert H
authors.initials: RH
authors.lastname: Grubbs