Premium
Asymmetric Synthesis of N ‐Fmoc‐( S )‐7‐aza‐tryptophan via Alkylation of Chiral Nucleophilic Glycine Equivalent
Author(s) -
Zou Yupiao,
Takeda Ryosuke,
Han Jianlin,
Konno Hiroyuki,
Moriwaki Hiroki,
Abe Hidenori,
Izawa Kunisuke,
Soloshonok Vadim A.
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100485
Subject(s) - chemistry , alkylation , glycine , nucleophile , pyridine , enantioselective synthesis , stereochemistry , nucleophilic addition , yield (engineering) , amino acid , combinatorial chemistry , tryptophan , chiral auxiliary , medicinal chemistry , organic chemistry , catalysis , biochemistry , materials science , metallurgy
Ni(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)‐1 H ‐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.