title: Ruthenium-catalyzed stereoselective intramolecular carbenoid C-H insertion for beta- and gamma-lactam formations by decomposition of alpha-diazoacetamides.
abstract: [reaction: see text] An operationally simple catalytic system based on [RuCl(2)(p-cymene)(2)] was developed for stereoselective cyclization of alpha-diazoacetamides by intramolecular carbenoid C-H insertion, and beta-lactams were produced in excellent yields and >99% cis-stereoselectivity. The Ru-catalyzed reactions can be performed without the need for slow addition of diazo compounds and inert atmosphere. With alpha-diazoanilides as substrate, the carbenoid insertion was directed selectively to aromatic C-H bond leading to gamma-lactam formation (>95% yield).
authors.affiliation: Department of Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong.
authors.forename: Matthew Kwok-Wai
authors.initials: MK
authors.lastname: Choi
authors.forename: Wing-Yiu
authors.initials: WY
authors.lastname: Yu
authors.forename: Chi-Ming
authors.initials: CM
authors.lastname: Che
mesh_terms: D002384:Catalysis; D003500:Cyclization; D003979:Diazonium Compounds / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis*; D015394:Molecular Structure; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003979:Diazonium Compounds; D007769:Lactams; C011752:diazoacetamide; D012428:Ruthenium