ChemInform Abstract: Sequential Nitromethane Conjugate Addition/Elimination-Pd-Catalyzed Allylation of β-Trifloxy Acrylates. Application to Carbapenem Synthesis.

Abstract

Sequential reactions of nitromethane via conjugate addition−elimination to β-trifloxy acrylates followed by Pd-catalyzed substitution of the resulting allyl nitro compounds with nucleophiles afforded homologation products at the β-position. 2-Naphthosultammethyl carbapenem, an anti-MRS carbapenem intermediate, was prepared in one pot from the corresponding 2-trifloxy compound. The scope and limitation of the one-pot method were investigated using several cyclic unsaturated esters and nucleophiles.