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On the basis of the results obtained from NMR spectroscopy, X-ray analysis and chemical transformations, it was established that acidic hydrolysis of (2S,4S)-4-arylaminoglutamates results in the formation of lactams in which ring closure occurs with the participation of the γ-amino and α-COOH groups; but isomeric lactams resulting from the participation

The paper describes the synthesis of ( 2S, 4S)-4-(N-Ts)- and ( 2S, 4S)-4-(N-Boc)-phenylamino-5-oxoprolines (pyroglutamic acid). These derivatives have been shown to be useful for synthesis of their amides and peptides in spite of steric hindrances caused by bulky groups adjacent to the reaction centre. Under the conditions applied no lactam ring opening and no loss of stereochemical integrity of any of the chiral centres were observed, which has been confirmed by NMR techniques.

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Reduction of the carbonyl groups in N‐protected (2S,4S)‐4‐amino‐5‐oxo‐1‐phenylprolinates with BH3 complexes resulted in (2S,4S)‐4‐aminoproline or (2S,4S)‐4‐aminoprolinol derivatives depending on the reaction conditions and the type of protecting groups used.

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