Novel synthesis of carbapenam by intramolecular attack of lactam nitrogen toward eta1-allenyl and eta3-propargylpalladium complex.
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).
Kozawa
Yuji
Y
Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.
Mori
Miwako
M
D015780:Carbapenems / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007769:Lactams / Q000737:chemistry; D008024:Ligands; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D010293:Pargyline / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry
D015780:Carbapenems; D007769:Lactams; D008024:Ligands; D009942:Organometallic Compounds; C482087:eta3-propargylpalladium; D010165:Palladium; D010293:Pargyline; D009584:Nitrogen