Substrate‐Controlled Synthesis of Functionalized Cyclohexanes with Four Stereocenters by Organocatalytic Asymmetric Domino Reactions Between γ‐Nitro Ketone and Enone

Abstract

AbstractOrganocatalytic asymmetric domino reactions of γ‐nitro ketones and enones have been developed for the construction of functionalized cyclohexane skeletons with four stereogenic carbon atoms, including one tetrasubstituted carbon stereocenter. 5‐Nitropentan‐2‐one and 6‐nitrohexan‐3‐one reacted with chalcone to afford six‐membered carbocycles with four consecutive stereocenters in yields of 51–91 % with 81–93 % ee and >20:1 dr. In addition, 4‐nitro‐1‐phenylbutan‐1‐one reacted with 4‐arylbut‐3‐en‐2‐ones to afford six‐membered carbocycles with two double consecutive stereocenters in yields of 59–92 % with 89–94 % ee and >20:1 dr. Interestingly, both four consecutive and nonconsecutive stereocenters could be constructed by these substrate‐controlled domino reactions.