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Borane Catalyzed Redox Isomerization of 2-Amino Chalcones: Hydride Abstraction or Hydride Migration?
European Journal of Organic Chemistry  (IF3.021),  Pub Date : 2021-08-19, DOI: 10.1002/ejoc.202100883
Rundong Zhou, Jan Paradies

The borane catalyzed redox isomerization of 2-amino chalocones was developed. Mechanistic investigations by kinetic, isotopic labelling, and competition experiments as well as computational studies corroborate the concerted [1,5] hydride shift as operative mechanism. The redox isomerization products are obtained in high yield and up to >95 : 5 diastereoselectivity.