Lipophilic NHC catalysis in aqueous medium was reported for the synthesis of biologically relevant (a)symmetrically substituted and unsymmetrically substituted syncarpamide analogues. All the reported reactions were performed in the absence of any expensive metal salts or additives. A diverse array of syncarpamide analogues was obtained in good yields. Lipophilic NHC catalysis was also extended to chemoselective transesterification reactions.