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

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• 作者：Zachary K. Wickens ; Kacper Skakuj ; Bill Morandi ; Robert H. Grubbs
• 刊名：Journal of the American Chemical Society
• 出版年：2014
• 出版时间：January 22, 2014
• 年：2014
• 卷：136
• 期：3
• 页码：890-893
• 全文大小：309K
• ISSN：1520-5126

文摘

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.