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Selective Isomerization via Transient Thermodynamic Control: Dynamic Epimerization of trans to cis Diols

Christian J. Oswood and David W. C. MacMillan*

*Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States, Email:

C. J. Oswood, D. W. C. MacMillan, J. Am. Chem. Soc., 2022, 144, 93-98.

DOI: 10.1021/jacs.1c11552

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The combination of hydrogen atom transfer photocatalysis and boronic acid mediated transient thermodynamic control enables a selective epimerization of cyclic trans diols to provide the less stable cis products. A range of substitution patterns and ring sizes are amenable to selective isomerization, including stereochemically complex polyols.

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reaction design of the selective epimerization

Key Words

cyclohexanols, cyclopentanols, diols, photochemistry

ID: J48-Y2022