DFT study on the structure and racemization mechanism of 2-amino-2 '-hydroxy-1,1 '-binaphthyl

摘要

To explore the structure of chiral ligands important in asymmetric catalysis, the density functional theory has been applied to study the ground-state geometries and isomerization processes of 2-amino-2 '-hydroxy-1,1 '-binaphthyl. The study shows that there are four isomers for 2-amino-2 '-hydroxy-1,1 '-binaphthyl, each of which has R- and S- enantiomer. The isomerization between R-conformations is easier than the racemization between R- and S- enantiomer. A parallel reaction mechanism via anti-enantiomerization routes was proposed for the racemization of 2-amino-2 '-hydroxy-1,1 '-binaphthyl, which provides a valuable reference for the design, synthesis, and resolution of chiral ligands.