Asymmetric Synthesis of N‐Fmoc‐(S)‐7‐aza‐tryptophan via Alkylation of Chiral Nucleophilic Glycine Equivalent

Abstract

AbstractNi(II)‐complexes, derived from glycine Schiff bases with chiral tridentate ligands, have been used as powerful tools for the synthesis of structurally diverse tailor‐made amino acids. In this manuscript, asymmetric alkylation reaction between chiral nucleophilic glycine derived Ni‐complex and 3‐(chloromethyl)‐1H‐pyrrolo[2,3‐b]pyridine has been developed under convenient conditions, which affords the corresponding alkylated Ni‐complex in 74 % yield and excellent diastereoselectivity (only one isomer). This reaction features convenient conditions and completely controlled diastereoselectivity, which provides a highly valuable approach for asymmetric synthesis of 7‐aza‐tryptophan.