Application of Oppolzer's Sultam in the Synthesis of Cyclic alfa-Amino Acids and beta-Amino Acids

• Autorzy: Woźniak D. , Szymańska A. , Ołdziej S. , Łankiewicz L. , Grzonka Z.
• Języki publikacji: EN

Abstrakty

EN

In this paper we describe the application of Oppolzer's sultam as a chiral auxiliary for the synthesis of cyclic alfa- and beta2-amino acids. The key step of the synthesis is stereoselective alkylation of sultam-derived glycine and beta-alanine Schiff's bases leading to diastereometrically pure products. Final compounds are obtained after mild acidic and next basic hydrolyses of auxiliary groups and can be directly converted into N-tert-butoxycarbonyl- or N-fluorenylmethoxycarbonyl derivatives useful in peptide synthesis. In the case of substrates alkylated with dihalogenoalkanes spontaneous cyclization occurring during removal of the auxiliary groups yields cyclic alfa-amino acids (proline homologues) with reasonable yield and stereoselectivity. Theoretical data explain the differences in tendency for cyclization between alfa- and beta-amino acids.

Słowa kluczowe

EN

amino acids; Oppolzer's sultam; diastereoselective alkylation; proline homologues

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2006
• Tom: Vol. 80, nr 2
• Strony: 265--277
• Opis fizyczny: Bibliogr. 27 poz.

Twórcy

autor

Woźniak D.

autor

Szymańska A.

autor

Ołdziej S.

autor

Łankiewicz L.

autor

Grzonka Z.

• Faculty of Chemistry, University of Gdańsk, Sobieskiego 18, 80-952 Gdańsk, Poland

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