Organic Chemistry Portal

Abstracts

Search:

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: dmacmillprinceton.edu

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

DOI: 10.1021/jacs.1c11552



see article for more reactions

Abstract

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.


see article for more examples

reaction design of the selective epimerization



Key Words

cyclohexanols, cyclopentanols, diols, photochemistry


ID: J48-Y2022