Access to 2-Oxoazetidine-3-carboxylic Acids Derivatives via Thermal Microwave-Assisted Wolff Rearrangement of 3-Diazotetramic Acids in the Presence of Nucleophiles

Submitting author affiliation:
Saint Petersburg State University, Saint Petersburg, Russian Federation

Beilstein Arch. 2024, 202435.

Published 04 Jun 2024

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In this work, we report an efficient approach to 2-oxoazetidine-3-carboxylic acid derivatives based on thermally promoted Wolff rearrangement of diazo tetramic acids 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 diazo tetramic acids leads exclusively to trans-diastereomeric β-lactams. The use of variously substituted diazo tetramic acids, including spirocyclic derivatives, as well as a wide range of nucleophiles provides access to a structural diversity of medically relevant 2-oxoazetidine-3-carboxylic acids amides and esters.

Keywords: β-lactams; Wolff rearrangement; diazo tetramic acids; nucleophiles; thermolysis; spirocycles

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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Lyutin, I.; Krivovicheva, V.; Kantin, G.; Dar'in, D. Beilstein Arch. 2024, 202435. doi:10.3762/bxiv.2024.35.v1

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