Work

Crystallization-Induced Diastereomer Transformations of Brominated Arylacetic and Arylpyruvic Acids

Year: 2025

Type: article

Abstract: Enantiopure halogenated carboxylic acid derivatives are valuable building blocks for the synthesis of stereochemically complex and pharmaceutically relevant molecules. We report the crystallization-induced diastereomer transformations (CIDTs) of diastereomeric salt pairs of α-bromo arylacetic and β-bromo arylpyruvic acids. The salts were obtained with high diastereoselectivities via direct filtration of the reaction mixture, and a salt break facilitated recovery of the enantiopure acids and chiral amines in high yields. The former react to produce synthetically useful enantiopure building blocks.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.5c02158

Authors: Susanna N. Angles, Alannah E. Miller, Jeffrey S. Johnson

Institution: University of North Carolina at Chapel Hill

Language: English

Topic: Crystallization and Solubility Studies

Subfield: Materials Chemistry

Field: Materials Science

Domain: Physical Sciences

Open Access status: green

Funders: National Institutes of Health, National Institute of General Medical Sciences

Awards: G6273545833, G7409528469, Synthesis of Bioactive Small Molecule Building Blocks