Chirality Control by Substituents in the Asymmetric Addition of Et_2Zn to Aromatic Aldehydes Catalyzed by cis-(1 R,2S)-2- Benzamidocyclohexanecarboxylic Acid Derived 1,3-Aminoalcohols

A series of novel optically active 1,3‐aminoalcohols based on cis‐(1R,2S)‐2‐benzamidocyclohexanecarboxylic acid and trans‐(1R,2R)‐2‐benzamidocyclohexanecarboxylic acid were synthesized and used in the asymmetric diethylzinc addition to aromatic aldehydes. Not only the enantioselectivity but also the stereochemistry of the product were controlled by the N‐substituents and the substituents on the vicinity carbon to hydroxyl group of the cis‐derivatives.