Solvent directed chemically divergent synthesis of β-lactams and α-amino acid derivatives with chiral isothiourea.

ABSTRACT: A protocol for the chemically divergent synthesis of β-lactams and α-amino acid derivatives with isothiourea (ITU) catalysis by switching solvents was developed. The stereospecific Mannich reaction occurring between imine and C(1)-ammonium enolate generated zwitterionic intermediates, which underwent intramolecular lactamization and afforded β-lactam derivatives when DCM and CH₃CN were used as solvents. However, when EtOH was used as the solvent, the intermediates underwent an intermolecular esterification reaction, and α-amino acid derivatives were produced. Detailed mechanistic experiments were conducted to prove that these two kinds of products came from the same intermediates. Furthermore, chemically diversified transformations of β-lactam and α-amino acid derivatives were a

SUBMITTER: Ji DS 

PROVIDER: S-EPMC8826511 | biostudies-literature | 2022 Feb

REPOSITORIES: biostudies-literature