A Straightforward and Convenient Synthesis of Cbz-Protected 2-(1-Aminoalkyl)oxazole-5-carboxylates

A Straightforward and Convenient Synthesis of Cbz-Protected 2-(1-Aminoalkyl)oxazole-5-carboxylates

Abstract Cbz-protected 2-(1-aminoalkyl)oxazole-5-carboxylates are readily obtainable by a two-step enantioselective sequence involving reaction of benzyloxycarbonyl protected amino acids with α-chloro-β-ketoesters and subsequent cyclization of the resulting acyloxyketones to required oxazoles upon t...

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Veröffentlicht in:Synlett 2005-08, Vol.2005 (13), p.2072-2076
Hauptverfasser: Trukhin, Dmitry V., Bagryanskaya, Irina Yu, Gatilov, Yuri V., Mikhalina, Tatiana V., Rogozhnikova, Olga Yu, Troitskaya, Tatiana I., Tormyshev, Victor M.
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Sprache:eng
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Zusammenfassung:Abstract Cbz-protected 2-(1-aminoalkyl)oxazole-5-carboxylates are readily obtainable by a two-step enantioselective sequence involving reaction of benzyloxycarbonyl protected amino acids with α-chloro-β-ketoesters and subsequent cyclization of the resulting acyloxyketones to required oxazoles upon treatment with neat ammonium trifluoacetate.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2005-871957