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Rhodium(III)-Catalyzed Asymmetric C-H Activation of N-Methoxybenzamide with Quinone and Its Application in the Asymmetric Synthesis of a Dihydrolycoricidine Analogue.

Xiaoqiang YanPeng ZhaoHao LiangHui XieJi-Jun JiangShaohua GouJun Wang
Published in: Organic letters (2020)
A chiral CpRhIII-catalyzed asymmetric C-H activation reaction of N-methoxybenzamides with quinones has been developed to efficiently forge chiral tricyclic hydrophenanthridinone scaffolds in ≤88% yield and ≤94% ee. With this methodology as the key step, an enantioenriched dihydrolycoricidine derivative has been synthesized in 64% overall yield in five steps.
Keyphrases
  • room temperature
  • solid state
  • ionic liquid
  • capillary electrophoresis