Lactams are often used as building blocks for antibiotics, such as penicillin. Now Hiroshi Matsubara, Ilhyong Ryu and colleagues have investigated an exciting radical route to produce them.
They show that acyl radicals can react as electrophiles in ionic type addition reactions with amines, which leads to cyclisation forming a series of lactams. Depending on the N-substituent (good or not good leaving group) reaction occurs via rare 1,4-H shift or via a formal homolytic substitution at nitrogen leading to interesting new compounds.
Download the paper now to read more about the synthetic scope and theoretical findings. It is free to access until 25th May.
This article will be included in the OBC special issue in memory of Athel Beckwith: Free Radical Chemistry. Coming soon
Radical carbonylation of ω-alkynylamines leading to α-methylene lactams. Synthetic scope and the mechanistic insights
Ilhyong Ryu, Takahide Fukuyama, Mami Tojino, Yoshitaka Uenoyama, Yuka Yonamine, Nozomi Terasoma and Hiroshi Matsubara
Org. Biomol. Chem., 2011, 9, 3780-3786
DOI: 10.1039/C1OB05145H
