A New General Access to α-Trifluoromethyl-Substituted Aromatic and Heteroaromatic α-Amino Acids

Article abstract of DOI:10.1055/s-1989-27408

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.