American Chemical Society
ja411749k_si_001.pdf (1.79 MB)

Catalyst-Controlled Wacker-Type Oxidation: Facile Access to Functionalized Aldehydes

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journal contribution
posted on 2014-01-22, 00:00 authored by Zachary K. Wickens, Kacper Skakuj, Bill Morandi, Robert H. Grubbs
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.