Synthesis and application of methyl itaconate–anthracene adducts in configuration assignment of chiral secondary alcohols by 1H NMR?

Organic & Biomolecular Chemistry Pub Date: 2021-09-16 DOI: 10.1039/D1OB01387D

Abstract

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.

Graphical abstract: Synthesis and application of methyl itaconate–anthracene adducts in configuration assignment of chiral secondary alcohols by 1H NMR
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