Beilstein J. Org. Chem.2024,20, 1894–1899, doi:10.3762/bjoc.20.164
191036, Russian Federation 10.3762/bjoc.20.164 Abstract In this work, we report an efficient approach to 2-oxoazetidine-3-carboxylic acid derivatives based on a thermally promoted Wolff rearrangement of diazotetramicacids in the presence of nucleophiles. The method allows easy variation of the
substituent in the exocyclic acyl group by introducing different N-, O-, and S-nucleophilic reagents into the reaction. The reaction of chiral diazotetramicacids leads exclusively to trans-diastereomeric β-lactams. The use of variously substituted diazotetramicacids, including spirocyclic derivatives, as
well as a wide range of nucleophiles provides access to a structural diversity of medically relevant 2-oxoazetidine-3-carboxylic acid amides and esters.
Keywords: β-lactams; diazotetramicacids; nucleophiles; spirocycles; thermolysis; Wolff rearrangement; Introduction
The importance of the β-lactam
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Graphical Abstract
Scheme 1:
Synthetic routes to 2-oxoazetidine-3-carboxylic acid derivatives.