Cobalt-Catalyzed Stereospecific C-N/C-O Bond Formation of Oxiranes with Diaziridines

Co-catalyzed stereospecific C-Nand C-O bond formationof oxiranes with diaziridines has been accomplished to furnish tetrahydro-[1,3,4]-oxadiazinesat room temperature. Optically active oxiranes can be coupled withhigh optical purities (>96% ee). Stereoselectivity, functionalgrouptolerance, mechanistic studies using DFT, and natural product modificationare the important practical features.

Automated summary

Stereospecific C-N and C-O bond formation of oxiranes with diaziridines has been achieved using a bimetallic catalyst at room temperature, resulting in the production of tetrahydro-[1,3,4]-oxadiazines. Optically active oxiranes can be coupled with high optical purities (>96% ee). The practical significance of this method lies in its stereoselectivity, tolerance for various functional groups, mechanistic studies using DFT, and potential application in natural product modification.