Cu-Catalyzed Tandem Oxidation-Intramolecular Cannizzaro Reaction of Biorenewables and Bioactive Molecules

ChemSusChem. 2024 Feb 20:e202400013. doi: 10.1002/cssc.202400013. Online ahead of print.ABSTRACTA tandem Cu-catalyzed oxidation-intramolecular Cannizzaro reaction leading to bioactive α-hydroxyesters from α-hydroxyketones is reported. The process uses oxygen as a sole oxidant to achieve the formation of glyoxals, which are efficiently converted in situ to important α-hydroxyesters. The mechanistic insights are provided by isotopic labeling and supported by DFT calculations. The transformation proved a robust synthetic tool to achieve the synthesis of human metabolites and hydroxyl esters of various biologically active steroid derivatives.PMID:38376915 | DOI:10.1002/cssc.202400013

Source: ChemSusChem - February 20, 2024 Category: Chemistry Authors: Hristo Petkov Martin Ravutsov Manuel Verganista Yavor Mitrev Nuno Candeias Svilen P Simeonov Source Type: research