Catalyst-controlled Wacker-type oxidation: facile access to functionalized aldehydes.

نویسندگان

  • Zachary K Wickens
  • Kacper Skakuj
  • Bill Morandi
  • Robert H Grubbs
چکیده

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.

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عنوان ژورنال:
  • Journal of the American Chemical Society

دوره 136 3  شماره 

صفحات  -

تاریخ انتشار 2014