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Synthesis 1988; 1988(2): 127-129
DOI: 10.1055/s-1988-27487
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Synthese von 2-(Methyl-trifluoracetylamino)-3-trimethylsiloxy-alkansäure- und N-Methyl-N-trifluoroacetyl-didehydroaminosäure-estern

Gerhard Simchen* , Dieter Schulz, Toni Seethaler
  • *Institut für Organische Chemie, Biochemie und Isotopenforschung der Universität Stuttgart, Pfalfenwaldring 55, D-7000 Stuttgart 80, Federal Republic of Germany
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Publication Date:
20 August 2002 (online)

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Synthesis of Methyl 2-(.Methyltrifluoroacetylamino)-3-(trimethylsiloxy)- alkanoates and N-Methyl-N-trifluoroacetyldidehydroamino Acid Methyl Esters Reaction of aliphatic and aromatic aldehydes 4 with the ketene acetal 3 in presence of Lewis acid 2 or zinc bromide affords methyl 2-(methyltrifluoroacetylamino)-3-(trimethylsiloxy)alkanoates 5. By elimination of trimethylsilanol from 5 by means of methanesulfonic acid anhydride or in presence of trifluoromethanesulfonic acid, 2-(methyltrifluoroacetylamino)-2-alkenoic esters (didehydroamino acid derivatives) 6 are obtained.