Diastereoselective Acylation of Racemic Heterocyclic Amines with N-Phthaloyl and N-Naphthaloyl (S)-Amino Acyl Chlorides: Possibility of Parallel Kinetic Resolution
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The acylative kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and 3,4-dihydro-3-methyl-2H-[1,4]benzoxazines with acyl chlorides of N-naphthaloyl-(S)-alanine and N-naphthaloyl-(S)-phenylalanine has been studied. It has been shown that diastereoselective acylation of racemic amines with N-naphthaloyl (S)-amino acyl chlorides results in the predominant formation of (R,S)-amides, whereas acylation of the same amines with N-phthaloyl (S)-amino acyl chlorides proceeds with the opposite diastereoselectivity. The parallel kinetic resolution of racemic 3,4-dihydro-3-methyl-2H-[1,4]benzoxazine using a mixture of acylating agents derived from a single precursor, (S)-phenylalanine, was carried out.
The work was supported by the Russian Science Foundation (project no. 14–13–01077). Equipment of the Center for Joint Use “Spectroscopy and Analysis of Organic Compounds” at the Postovsky Institute of Organic Synthesis, UB RAS, was used.
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