Ligand-Controlled Asymmetric Conjugate Addition of Lithium Amides

Significance

Chiral β-amino acids are common structural units, present in a variety of biologically active molecules. Herein, the authors applied an efficient tandem asymmetric nucleophilic addition-enolate alkylation process for the synthesis of some representative β-amino acids. A recoverable chiral diether serves as a chirality source. The authors have also developed a new original method for the cleavage of a benzyl protection group, useful in the cases where usual hydrogenation or oxidation protocols are not suitable. The utility of the methodology is demonstrated by the synthesis of some industrially important intermediates.