Cobaltaelectro-Catalyzed C–H Annulation with Allenes for Atropochiral and P-stereogenic Compounds: Late-stage Diversification and Continuous Flow Scale up

05 May 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The 3d metallaelectro-catalyzed C–H activation has been identified as an increasingly viable strategy to access valuable organic molecules in a sustainable fashion under exceedingly mild reaction conditions. However, the development of enantioselective 3d metallaelectro-catalyzed C–H activation is very challenging and in its infancy. Here, we disclose the merger of cobaltaelectro-catalyzed C–H activation with asymmetric catalysis for the highly enantioselective annulation of allenes. A broad range of C–N axially chiral and P-stereogenic compounds were thereby obtained in good yields of up to 98% with excellent enantioselectivities of up to >99% ee. The practicality of this approach was demonstrated by the diversification of complex bioactive compounds and drug molecules as well as decagram-scale enantioselective electrocatalysis in continuous flow.

Keywords

Asymmetric catalysis
C–H activation
Cobalt
Electrochemistry
Axial chirality
P-chirality

Supplementary materials

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