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
Keywords
aziridines - β-lactams - kinetic resolution - enantiospecific - stereospecific
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.
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.
