Volume 27, Issue 18
Natural Products
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ChemInform Abstract: Synthesis of α-Trifluoromethyl Substituted α-Amino Acid Derivatives from Methyl 3,3,3-Trifluoro-2-diazopropionate.

S. N. OSIPOV

S. N. OSIPOV

Inst. Org. Chem., Univ. Leipzig, D-04103 Leipzig, Germany

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N. SEWALD

N. SEWALD

Inst. Org. Chem., Univ. Leipzig, D-04103 Leipzig, Germany

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A. F. KOLOMIETS

A. F. KOLOMIETS

Inst. Org. Chem., Univ. Leipzig, D-04103 Leipzig, Germany

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A. V. FOKIN

A. V. FOKIN

Inst. Org. Chem., Univ. Leipzig, D-04103 Leipzig, Germany

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K. BURGER

K. BURGER

Inst. Org. Chem., Univ. Leipzig, D-04103 Leipzig, Germany

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First published: April 30, 1996

Abstract

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ChemInform Abstract

Catalyzed decomposition of 3,3,3-trifluoro-2-diazopropionate (II) in the presence of the teriary amines (I) provides a new one-step procedure for the preparation of α-CF3-containing α-amino acids (III) via an (1,2)-Stevens rearrangement of the initially formed ylides. The ylides obtained from the interaction of (II) with the N-H nucleophiles (IV) form α-trifluoroalanines (V) via hydrogen migration.

chemical structure image

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