BINOL as a Chiral Solvating Agent for Sulfiniminoboronic Acids.

ABSTRACT: ¹H NMR spectroscopic studies using BINOL as a chiral solvating agent (CSA) for a scalemic sulfiniminoboronic acid (SIBA) have revealed concentration- and enantiopurity-dependent variations in the chemical shifts of diagnostic imine protons used to determine enantiopurity levels. ¹¹B/¹⁵N NMR spectroscopic studies and X-ray structural investigations revealed that unlike other iminoboronate species, BINOL-SIBA assemblies do not contain N-B coordination bonds, with ¹H NMR NOESY experiments indicating that intermolecular H-bonding networks between BINOL and the SIBA analyte are responsible for these variations. These effects can lead to diastereomeric signal overlap at certain er values that could potentially lead to enantiopurity/configuration misass

SUBMITTER: Groleau RR 

PROVIDER: S-EPMC10666087 | biostudies-literature | 2023 Nov

REPOSITORIES: biostudies-literature