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

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Morandi,  Bill
old and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States;
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Wickens, Z. K., Skakuj, K., Morandi, B., & Grubbs, R. H. (2014). Catalyst-Controlled Wacker-Type Oxidation: Facile Access to Functionalized Aldehydes. Journal of the American Chemical Society, 136(3), 890-893. doi:10.1021/ja411749k.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0025-BAB2-9
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.