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Kinetic Resolution of Racemic Amino Alcohols through Intermolecular Acetalization Catalyzed by a Chiral Brønsted Acid
The kinetic resolution of racemic
secondary alcohols is a fundamental
method for obtaining enantiomerically enriched alcohols. Compared
to esterification, which is a well-established method for this purpose,
kinetic resolution through enantioselective intermolecular acetalization
has not been reported to date despite the fact that the formation
of acetals is widely adopted to protect hydroxy groups. By taking
advantage of the thermodynamics of acetalization by the addition of
alcohols to enol ethers, a highly efficient kinetic resolution of
racemic amino alcohols was achieved for the first time and in a practical
manner using a chiral phosphoric acid catalyst