Different chiral and achiral oxazolidinones were tested. The Nacylation of chiral oxazolidinones substituted at C-4 position (compounds 25-28) gave products in good yields. Due to the steric nature of the substituents, the reaction required an elevation of reaction temperature (60 °C) and a slight increase of equivalents of base. Reaction between the C-5 substituted oxazolidinone and cinnamaldehyde was able to deliver the product 29 in 73% yield under normal reaction condition, leaving the primary alkyl chloride unscathed. Furthermore, it was also possible to incorporate 2-pyrrolidinone as nucleophile for the synthesis of two natural products, Piperlotine F and Piperlotine G, an Nrf2 activator, in moderate to good yields. The postulated catalytic cycle (Scheme 4) starts with deprotonation of the NHC-precatalyst forming the active carbene species I. The catalyst then adds to cinnamaldehyde 1 to give Breslow intermediate II. With the help of the linked ETMsystem, the Breslow intermediate is subsequently oxidized by O2 via a multistep electron transfer step, to form the acyl azolium intermediate III. In the last step, the deprotonated oxazolidinone IV reacts with acyl azolium III forming 3 and regenerating the catalyst.