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Forging structural complexity: diastereoselective synthesis of densely substituted β-lactams with dual functional handles for enhanced core modifications.

ABSTRACT: The preparation of the β-lactam motif containing both C-Br and N-O bonds as functional handles remains an unmet synthetic challenge. Described herein is a novel and highly diastereoselective NBS-mediated cyclization of N-alkoxy α,β-unsaturated silyl imino ethers to furnish nearly three dozen α-bromo N-alkoxy β-lactams. The reaction gives rapid and convenient access to structurally diverse monocyclic, spirocyclic and fused β-lactams in moderate to good yields. The two functional handles were shown to be useful for the further elaboration of the β-lactam core.

SUBMITTER: Rodriguez Trevino AM

PROVIDER: S-EPMC11332334 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature

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Forging structural complexity: diastereoselective synthesis of densely substituted β-lactams with dual functional handles for enhanced core modifications.

Rodriguez Treviño Agustin M AM Loch-Temzelides Pierre P Pandiri Sanjay S Kirkland Justin K JK Davenport Michael T MT Aguinaga Ulises U Yousufuddin Muhammed M Ess Daniel H DH Kürti László L

Chemical science 20240808

The preparation of the β-lactam motif containing both C-Br and N-O bonds as functional handles remains an unmet synthetic challenge. Described herein is a novel and highly diastereoselective NBS-mediated cyclization of <i>N-</i>alkoxy α,β-unsaturated silyl imino ethers to furnish nearly three dozen α-bromo <i>N</i>-alkoxy β-lactams. The reaction gives rapid and convenient access to structurally diverse monocyclic, spirocyclic and fused β-lactams in moderate to good yields. The two functional han ...[more]

PMID: 39170719

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