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Synfacts 2025; 21(03): 278
DOI: 10.1055/a-2518-2932
DOI: 10.1055/a-2518-2932
Metals in Synthesis
Enantio- and Stereospecific Synthesis of β-Lactams via Ring Expansion of Aziridines under Rhodium Catalysis
Calet S,
Urso F,
Alper H *.
University of Ottawa, Canada
Enantiospecific and Stereospecific Rhodium(I)-Catalyzed Carbonylation and Ring Expansion of Aziridines. Asymmetric Synthesis of β-Lactams and the Kinetic Resolution of Aziridines.
J. Am. Chem. Soc. 1989;
111: 931-934
DOI: 10.1021/ja00185a023
Enantiospecific and Stereospecific Rhodium(I)-Catalyzed Carbonylation and Ring Expansion of Aziridines. Asymmetric Synthesis of β-Lactams and the Kinetic Resolution of Aziridines.
J. Am. Chem. Soc. 1989;
111: 931-934
DOI: 10.1021/ja00185a023
Significance
The β-lactam moiety is commonly found in biologically active compounds. Alper and co-workers reported a Rh-catalyzed ring expansion of aziridines in a CO atmosphere to access β-lactams regioselectively.
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Comment
The authors showed that the reaction is both stereospecific and enantiospecific. Utilizing L-menthol as a chiral additive resulted in a kinetic resolution, generating the desired β-lactam in excellent optical purity.
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Publication History
Article published online:
25 February 2025
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