Abstract Cram model and Felkin-Ahn model have been applied to predict the stereoselectivity in the addition of nucleophiles to α-chiral carbonyl compounds. However, rare publications explain how to understand the two models thoroughly. Herein, based on conformation of carbonyls, three different situations are introduced: non heteroatom at the chiral center, a heteroatom at the chiral center without chelation and metal ion or proton capable of chelation with the heteroatom and carbonyl oxygen. Stepwise approach is introduced to predict the final configurations of products here, which is understandable and memorable.
SHEN Qi, XU Jia-Shi, CHEN Xiao-Dan. Stereoselectivity in the Nucleophile Addition of Acyclic α-Chiral Carbonyl Compounds[J]. Chinese Journal of Chemical Education, 2022, 43(2): 120-124.
