4.1 Article

Kinetic resolution of heterocyclic amines by reaction with optically active acid chlorides.: The effect of reaction conditions on the diastereoselectivity of acylation of (±)-3-methyl-2,3-dihydro-4H-1,4-benzoxazine

Journal

RUSSIAN CHEMICAL BULLETIN
Volume 53, Issue 6, Pages 1253-1256

Publisher

SPRINGER
DOI: 10.1023/B:RUCB.0000042282.29765.2f

Keywords

kinetic resolution of racemates; 3-methyl-2,3-dihydro-4H-1,4-benzoxazine; acid chlorides; (S)-naproxen; N-tosyl-(S)-proline; acylation

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The influence of the reaction conditions (solvent, base) on the diastereoselectivity of acylation of (+/-)-3-methyl-2,3-dihydro-4H-1,4-benzoxazine with (S)-naproxen and N-tosyl(S)-proline chlorides was studied. The highest diastereoselectivity was observed for the reaction carried out in benzene in the presence of aliphatic tertiary amines.

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