Organic Chemistry

Reverse Regioselectivity in Reductive Ring Opening of Epoxide Enabled by Zirconocene and Photoredox Catalysis


A ring opening of epoxide with zirconocene and photoredox catalysis has been developed. Compared to the ring opening methods with titanocene, the present protocol exhibited reverse regioselectivity to afford more-substituted alcohols via putative less-stable radicals. DFT calculations indicated that the observed regioselectivity could be explained by shifting the transition states to more reactant-like structures by changing the metal center of the metallocene catalyst.


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Supplementary material

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