Stereochemical Studies. LII. Studies on the Stereochemical Courese in Deaminative Bromination of 3, 5-Dichloro-L-tyrosine and in Amination of the Corresponding α-Bromo Acid. Existence of Strong Neighboring "Phenoxide"Group Participation

抄録

It has become apparent that deaminative bromination of 3, 5-dichloro-L-tyrosine (L-4) to the corresponding α-bromo acid ((-)-5) occurs with retention of configuration, and that amination of this bromo acid to the starting amino acid (L-4) occurs also with retention of configuration. The unusual stereochemical course in this amination step was found to be due to the strong neighboring aryl group participation as a phenoxide form.