161972-09-4Relevant articles and documents
Catalyst-controlled wacker-type oxidation: Facile access to functionalized aldehydes
Wickens, Zachary K.,Skakuj, Kacper,Morandi, Bill,Grubbs, Robert H.
supporting information, p. 890 - 893 (2014/02/14)
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.