When a THF solution of beta-lactam having propargyl phosphate was warmed in the presence of 5 mol % of Pd(2)(dba)(3) x CHCl(3), 20 mol % of a bidentate ligand, and sodium acetate (1.5 equiv) at 40 degrees C for 22 h, carbapenam was produced in high yield. In this reaction, the lactam nitrogen attacked the central carbon of a eta(3)-propargylpalladium complex, which was formed from propargyl phosphate and Pd(0).

Carbapenam is a very important skeleton of beta-lactam antibiotics, and it has a highly strained structure. When enynes 9 were treated with RuH(2)CO(PPh(3))(3) (10 mol %) in toluene upon heating, carbapenams 10 were obtained in good yields.

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3-alkoxycarbonyl-1beta-methylcarbapenem could be synthesized by using a palladium-catalyzed C-N bond-forming reaction between vinyl halide and beta-lactam nitrogen. In this reaction, the use of Pd(OAc)(2) and DPEphos gave a good result, and the generation of Pd(0) from Pd(OAc)(2) in the absence of a base is necessary to increase the yield.

No abstract