Ruthenium-catalyzed stereoselective intramolecular carbenoid C-H insertion for beta- and gamma-lactam formations by decomposition of alpha-diazoacetamides.

[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).