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

ZK Wickens, K Skakuj, B Morandi…

Index: Wickens, Zachary K.; Skakuj, Kacper; Morandi, Bill; Grubbs, Robert H. Journal of the American Chemical Society, 2014 , vol. 136, # 3 p. 890 - 893

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Citation Number: 34

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 ...