期刊
TETRAHEDRON-ASYMMETRY
卷 22, 期 2, 页码 185-189出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2010.12.017
关键词
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资金
- Russian Foundation for Basic Research [10-03-00084]
- Russian Federation [NSh 65261.2010.3]
- Ural Division of RAS [09-P-3-2001, 09-1-3-2004]
- [02.522.12.2011]
The acylative kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and 2,3-dihydro-3-methyl-4H-1,4-benzoxazine using acyl chlorides of N-phthaloyl-(S)-phenylalanine, N-phthaloyl-3-(4-nitrophenyl)-(S)-alanine and N-phthaloyl-O-methyl-(S)-tyrosine as chiral resolving agents has been carried out. It is shown that the effectiveness of an acylative kinetic resolution depends on the electronic effects of substituents in the phenyl fragment of the acylating agent and increases as the electron-donating properties of the para-substituent (OMe > H > NO2) in phenyl fragment of N-phthaloyl-3-aryl-(S)-alanyl chlorides increase; conducting the process at a reduced temperature also contributes to an enhancement of the kinetic resolution. (C) 2010 Elsevier Ltd. All rights reserved.
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