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1 2006

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Activation of N-Benzoyl-2-substituted-2-hydroxymethyl-2-amino Acids with Chiral Coupling Reagents Prepared in situ from 2-Chloro-4,6-dimethoxy-1,3,5-triazine

Kolesińska B., Kamińska J., Miyazawa T., Kamiński Z.

Polish Journal of Chemistry

2006

Vol. 80, nr 11

1817-1824

Chiral triazine condensing reagents were obtained in situ by treatment 2-chloro-4,6-dimethoxy-1,3,5-triazine with strychnine, brucine, sparteine, nicotine and quinine, and used for enantioselective activation of racemic N-benzoyl derivatives of 2-methylserine, 2-isobutylserine and 2-benzylserine affording enantiomerically enriched appropriate 2-phenyl-4-hydroxymethyl-4-substituted-1,3-oxazolin-5-one. Configuration and ee of products were determined by HPLC on chiral stationary phase. S configuration of enantiomer activated faster to oxazolinone was confirmed for all chiral amines except quinine. For the later amine, R enantiomer of N-benzoyl-2-methylserine was activated faster. For experiments involving strychnine as chiral auxiliary, enantiomeric enrichmentwas substantially lower than in the case of proteinogenic amino acids and increased with the size of C alfa-substituent from 12% ee for methyl to 36% ee for isobutyl side chain.