Direct Catalytic Enantioselective Reaction of α-Isocyanoacetonitriles with Ketimines Using Cinchona Alkaloid Amide-Cu(II) Catalysts.

Abstract

The first enantioselective reaction of α-isocyanoacetonitriles was developed. The reaction of various α-isocyanoacetonitriles with ketimines using cinchona alkaloid amide-Cu(II) catalysts afforded imidazolines with consecutive tetrasubstituted stereogenic carbon centers in good yields and high diastereo- and enantioselectivities. The stereoselectivity of the reaction is explained on the basis of the control experiment and density functional theory (DFT) calculations. The products were subsequently converted into chiral compounds. This process highlights the possible use of α-isocyanoacetonitriles for asymmetric and organic syntheses.