Year: 2025
Type: article
Abstract: A ruthenium‐catalyzed intramolecular carbenoid insertion into a C(sp3)H bond leads to the enantioselective formation of chiral β‐lactams. The reaction is catalyzed by a ruthenium complex featuring a chiral pyridine‐2,6‐bis(oxazoline) ligand, combined with a cyclometalated phenylimidazo[1,5‐a]pyridine ligand. This complex belongs to a recently introduced new class of ruthenium catalysts (Angew. Chem. Int. Ed. 2020, 59, 12393). Starting from N‐benzyl α‐diazoacetamides, chiral β‐lactams are provided in up to 82% isolated yield with up to 98% enantiomeric excess, without any occurrence of a Buchner side reaction. Mechanistic experiments reveal that β‐lactam (4‐membered ring) formation is inherently favored over the more common γ‐lactam (5‐membered ring) formation.
Authors: Anna Lena Opper, Xin Nie, Sergei I. Ivlev, Eric Meggers
Institution: Philipps University of Marburg
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,330
Funder: Philipps-Universität Marburg
OpenAlex ID: W4409482786