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Enamine/imine tautomerism in α,β-unsaturated-α-amino acids

1998; Elsevier BV; Volume: 54; Issue: 50 Linguagem: Inglês

10.1016/s0040-4020(98)00908-9

1464-5416

S.‐P. LU, Anita H. Lewin,

Synthesis of β-Lactam Compounds

Investigation of the α,β-unsaturated-α-amino acids—dehydrovaline, dehydrophenylalanine, and dehydropipecolinic acid—revealed that these compounds undergo rapid hydrolysis in neutral aqueous medium, via the imine tautomers, even when the corresponding esters and sodium salts exist as the enamine tautomers. This is true even for dehydropipecolinic acid which had been reported to be stable for 10–18 h in dilute aqueous neutral solution.