Diastereoselective palladium(0)-catalyzed reactions of lithium enolates of chiral N-acyloxazolidinones. Asymmetric synthesis of 2-substituted (E)-4- alkylidenepentanedioates

Article abstract of DOI:10.1016/0040-4039(95)01043-h

The palladium(0)-catalyzed reactions of lithium enolates 1 of N- acyloxazolidinones with 3-acetoxy-2-methylenealkanoates 2, easily prepared via DABCO-catalyzed coupling of corresponding aldehydes with acrylates, proceeded diastereoselectively and regioselectively to give chiral N-((E)-4- alkoxycarbonyl-4-pentenoyl)oxazolidinones 3, useful intermediates of metallopeptidase inhibitors.