β-Lactams are structural motifs commonly found in antibiotics and other biologically relevant molecules. The ring strain associated with these compounds also makes them particularly valuable as synthetic intermediates through various ring-opening processes. Efficient syntheses of such motifs are thus highly desirable in the pharmaceutical industry. Other [3+1] strategies to β-lactams typically require harsh reaction conditions, use unstable cyclopropanone precursors, and result in lower yields over multiple steps. In this work, we report a simple and mild approach for their formation using readily available cyclopropanone precursors via a metal-catalyzed formal [3+1] cycloaddition. An intramolecular version of the transformation is also explored, leading to the rapid elaboration of carbapenems commonly used for the treatment of bacterial infections.

Synthesis of β-lactams via metal-catalyzed formal [3+1] cycloaddition of cyclopropanones

2019 Fall National Meeting

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