Ruthenium-catalyzed stereoselective intramolecular carbenoid C-H insertion for beta- and gamma-lactam formations by decomposition of alpha-diazoacetamides |
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Authors: | Choi Matthew Kwok-Wai Yu Wing-Yiu Che Chi-Ming |
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Institution: | 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. |
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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). |
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