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ChemInform Abstract: Fluorosubstituted Amino Acids. Part 5. Imines of Trifluoropyruvic Acid in the Synthesis of N-Substituted Trifluoroalanines.
Abstract
The compounds (III) and (VII) are prepared by Staudinger reaction between the keto ester (I) and the phosphazenes (II) or by condensation of (I) with (D,L)-phenylethylamine (VI).
ChemInform Abstract
The compounds (III) and (VII) are prepared by Staudinger reaction between the keto ester (I) and the phosphazenes (II) or by condensation of (I) with (D,L)-phenylethylamine (VI). The compounds (IIIa) are already known, (IIIb) and (VII) are prepared for the first time. (IIIa) and (VII) are converted to the N-substituted trifluoroalanine derivatives (IVa) or (VIII) by treatment with Zn/AcOH. The imine (IIIb) does not react with Zn/AcOH. On treatment with a base the imines (IIIb) and (VII) undergo 1,3-protic shifts to afford the products (V) or (IX).
