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Synthesis 1989; 1989(11): 850-855
DOI: 10.1055/s-1989-27408
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Ein newer allgemeiner Zugang zu α-trifluormethyl-substituierten aromatischen und heteroaromatischen α-Aminosäuren

Klaus Burger* , Karl Gaa, Klaus Geith, Christian Schierlinger
  • *Institut für Organische Chemie der Technischen Universität München, Lichtenbergstr. 4, D-8046 Garching, Federal Republic of Germany
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Publication Date:
02 May 2002 (online)

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A New General Access to α-Trifluoromethyl-Substituted Aromatic and Heteroaromatic α-Amino Acids Syntheses of α-trifluoromethyl substituted heteroarylglycine and phenylalanine derivatives 7 bzw. 12a from 5-fluoro-2-phenyl-4-trifluoromethyloxazole (2) are described. The key step of the new method is a 1,3-benzyl shift from oxygen to carbon. The isolation of mixed products in "cross experiments"in the phenylalanine series supports the notion that the 1,3-benzyl shift is not a 1,3-sigmatropic process.