Abstract
A comparative study of the kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and 2,3-dihydro-3-methyl-4 H-1,4-benzoxazine using N-phthaloyl-( S)-amino acyl chlorides as chiral acylating agents is described. Temperature and solvent effects on the stereochemical features have been examined. It has been found that N-phthaloyl-( S)-phenylalanyl and N-phthaloyl-( S)-2-phenylglycyl chlorides bearing aromatic substituents close to the stereogenic centre are more stereoselective acylating agents than N-phthaloyl-( S)-alanyl chloride. For the preparative kinetic resolution of racemic amines N-phthaloyl-( S)-phenylalanyl chloride proved to be the most appropriate chiral acylating agent.
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