Enantiodivergent Reaction of Ketimines with Malononitriles Using Single Cinchona Alkaloid Sulfonamide Catalysts

Abstract

Abstract We report the enantiodivergent reaction of ketimines derived from α‐ketoesters with malononitriles using a single chiral source. The reactions using an 8‐quinolinesulfonyl cinchona alkaloid catalyst in the presence and absence of Et 2 Zn gave both enantiomers in high yields with high enantioselectivities (53∼99% yield, 99:1∼3:97 er). The obtained malononitrile‐derived α‐amino acids were converted into various optically active compounds. A reaction mechanism is proposed to explain the observed enantiodivergency. magnified image