Abstract
Two methods were investigated for the preparation of six chiral α-bromonitriles with different optic purities. The nitrous deamination of amino acids gives α-bromoacids, which react with chlorosulfonyl isocyanate followed by triethylamine to afford α-bromonitriles with moderate enantiomeric excess. However, the dehydration of corresponding α-bromoamids using thionyl chloride gives α-bromonitriles with good enantiomeric excess up to 94%. The use of phosphoryl chloride instead of thionyl chloride results in more than 30% racemization as determined by high-performance liquid chromatograpic analysis.
GRAPHICAL ABSTRACT
ACKNOWLEDGMENT
The authors thank the Direction Générale de la Recherche Scientifique of the Tunisian Ministry of Higher Education and Scientific Research for the financial support of this research.