Rapid and Highly Diastereoselective Synthesis of α-Bromo N-Alkoxy β-Lactams from α,β-Unsaturated Silyl Imino Ethers

15 December 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


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 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.


silyl imino ethers
NBS-mediated cyclization

Supplementary materials

Full Supporting Information
Contains the characterization data for all the compounds.


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