Journal
RUSSIAN CHEMICAL BULLETIN
Volume 60, Issue 5, Pages 948-954Publisher
SPRINGER
DOI: 10.1007/s11172-011-0149-0
Keywords
kinetic resolution; 2-arylpropionic acids; acyl chlorides; acylation; 3-methyl-2,3-dihydro-4H-[1,4]benzoxazine; naproxen; ibuprofen; carboxamides; amines; enantiomers; diastereoselectivity
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Funding
- Russian Foundation for Basic Research [10-03-00084]
- Council on Grants at the President of the Russian Federation [NSh-65261.2010.3]
- Ural Branch of the Russian Academy of Sciences [09-P-3-2001, 09-I-3-2004]
- Ministry of Education and Science of the RF [02.522.12.2011]
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Kinetic resolution of racemic 3-methyl-2,3-dihydro-4H-[1,4]benzoxazines in the reaction with chiral 2-arylpropionyl chloride predominantly yielded R*,R*-diastereomers. Ibuprofen acyl chloride as acylating agent was found to be more selective and sensitive to the changes in the reaction temperature as compared to naproxen acyl chloride and 2-phenylpropionyl chloride.
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