RESUMO
Correction for 'Synthesis and application of methyl itaconate-anthracene adducts in configuration assignment of chiral secondary alcohols by 1H NMR' by Puracheth Rithchumpon et al., Org. Biomol. Chem., 2021, DOI: 10.1039/D1OB01387D.
RESUMO
Novel chiral derivatising agents (CDAs) such as methyl itaconate-anthracene adducts (MIAs) were reported for the absolute configuration determination of chiral secondary alcohols by the 1H NMR technique. These adducts were facilely prepared through well-known reactions, and furthermore, commercially available starting materials. According to these synthetic routes, the desired MIAs were afforded in 6 steps with 49% overall yield from dimethyl itaconate. Moreover, the represented MIAs provided significantly large differences of chemical shift values (ΔδSR). No racemisation from the tertiary characteristics of the adjacent alpha carbon was observed.
RESUMO
New alternative chiral derivatizing agents, ß-keto-anthracene adducts (KAAs), were accomplished and the influence of aromatic moieties at the α-carbon position for elucidation of the absolute configuration of chiral secondary alcohols via NMR was studied. The α-benzoyl substituted KAAs strongly enhance the anisotropic effect which produced greater ΔδRS values than other conventional reagents. We propose a simplified model to describe the conformations and to assign the absolute configuration in several chiral alcohol samples.