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Highly Enantioselective [2+2+2] Cycloaddition of Enediynes Enabled by Cobalt/Organophotoredox Cooperative Catalysis

Takeshi Yasui, Rine Tatsumi, Yoshihiko Yamamoto

2021ACS Catalysis31 citationsDOIOpen Access PDF

Abstract

Herein, we report dual cobalt and photoredox catalysis enabled [2+2+2] cycloaddition of enediynes to produce tricyclic cyclohexadienes bearing a quaternary bridgehead carbon. A variety of enediynes were used, and the corresponding cyclohexadienes were obtained in good to high yields. The use of a chiral ligand, (S)-Segphos, enabled a highly enantioselective reaction allowing access to highly enantio-enriched cyclohexadienes.

Topics & Concepts

Enantioselective synthesisCobaltCycloadditionCatalysisChemistryCombinatorial chemistryLigand (biochemistry)Organic chemistryReceptorBiochemistryCatalytic Alkyne ReactionsCyclization and Aryne ChemistryCatalytic C–H Functionalization Methods
Highly Enantioselective [2+2+2] Cycloaddition of Enediynes Enabled by Cobalt/Organophotoredox Cooperative Catalysis | Litcius