First iodine/IL-catalyzed carbohydrate activation as aldehyde equivalent for [C+2C+N] construction of β-lactam ring

Selective Functionalizations of Cycloalkene‐Fused β‐Lactams and their Transformations into Densely‐Substituted Three‐Dimensional Molecular Entities

“…Then, in a subsequent diastereoselective ringclosing step, cis-β-lactams 4 were formed (Scheme 1). [8] Radical cyclization is also used as a preparation method for the synthesis of β-lactams. [9] The Grainger group reported a protocol for the preparation and functionalization of β-lactams by bond formation at the C2À C3 position.…”

“…Then, in a subsequent diastereoselective ring‐closing step, cis ‐β‐lactams 4 were formed (Scheme 1). [8] …”

Conformationally constrained fused bicyclic iminosugars: synthetic challenges and opportunities

“…TEMPO-like oxidation of the free primary alcohol using 216 triggered the formation of a hemiaminal intermediate which was further oxidized to a δ-lactam, thus providing bicyclic dilactam 217 in 87% yield. 105 Unprotected carbohydrates, 2-phenyl-2-oxazolan-5-one 218, and aromatic amines were used as one carbon, two carbons and nitrogen sources, respectively. In this process, imidazolium hydroxide-mediated deprotonation of 218 is expected to trigger a Mannich-type reaction affording adducts 221.…”