Stereochemical Studies. LX. Neighboring Phenyl Group Participation. I. Stereospecific Transformation of L-Phenylalanine to Optically Active Tropic Acid

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Trifluoroacetolysis of (S)-3-phenyllactic acid ester sulfonate ((S)-7), obtained from L-phenylalanine via nitrous acid deamination followed by ethanolysis, afforded (R)-tropic acid ester ((R)-8) in good yield by phenyl migration with inversion, while acetolysis followed by ethanolysis afforded (R)-phenyllactic acid ester ((R)-6b) in good yield by substitution with inversion. Mechanistic aspects of these reactions are discussed.