ChemInform Abstract: Regioselective Palladium-Catalyzed Amination of 4-Chloroacetoxyalk-2enoic Esters: Synthesis of Pyrrol-2(5H)-ones (4-But-2-enelactams).

ChemInform Abstract

The aldehydes (I) are coupled with methyl p-chlorophenylsulfinylacetate (II) to give the E-hydroxyalkenoates (III). Chloroacetylation of (III) and subsequent amination with the primary amines (VI) in the presence of a Pd(0) catalyst lead to the formation of the unsaturated amino esters (VII) which react with benzenethiol (VIII), yielding the lactams (IX). These are converted into the butenelactams(X) by peracid oxidation and subsequent elimination.