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

• Autorzy: Kolesińska B. , Kamińska J. , Miyazawa T. , Kamiński Z.
• Języki publikacji: EN

Abstrakty

EN

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.

Słowa kluczowe

EN

2-methylserine; 2-isobutylserine; 2-benzylserine; enantioselective activation; 2-chloro-4,6-dimethoxy-1,3,5-triazine

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2006
• Tom: Vol. 80, nr 11
• Strony: 1817--1824
• Opis fizyczny: Bibliogr. 21 poz., rys.

Twórcy

autor

Kolesińska B.

autor

Kamińska J.

autor

Miyazawa T.

autor

Kamiński Z.

• Institute of Organic Chemistry, Łódź University of Technology, Żeromskiego 116, 90-924 Łódź, Poland

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