Diasteroseletive Synthesis of Functionalized Cyclohexanones by Condensation of Acetoacetanilide and Various Aldehydes in the Presence of DMAP as Catalyst

Functionalized cyclohexanones containing stereogenic centers as valuable building blocks arepresent at the core of an array of natural products candidates [1], that they are biologicallyactive agents with antibacterial, and anticancer properties [2]. In this context, and in continuationof our previuos work [3], we reported a facial synthetic strategy for the diasteroselectivesynthesis of N,Nʼ-diaryl-2-hydroxy-6-methyl-4-oxocyclohexane-1,3-dicarboxamide usingDMAP as catalyst. Acetoacetanilide undergoes a diasteroselective condensation reaction withvarious aromatic aldehydes in EtOH at 50 °C to afford desirable products via one-pot pseudothree-component reaction. The present protocol provides an inexpensive and efficient route toobtain functionalized cyclohexanones containing four quartetnary stereogenic centers withhigh yields from the simple and readily available starting materials undermild conditions inshorter reaction times. The products have been characterized by spectral data.