Asymmetric Synthesis of N-Fmoc-(S)-7-aza-tryptophan via Alkylation of Chiral Nucleophilic Glycine Equivalent
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-(chl...
| Authors: | , , , , , , , |
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| Format: | article |
| Publication Date: | 2021 |
| Country: | España |
| Institution: | Universidad del País Vasco |
| Repository: | Addi. Archivo Digital para la Docencia y la Investigación |
| OAI Identifier: | oai:addi.ehu.eus:10810/52919 |
| Online Access: | http://hdl.handle.net/10810/52919 |
| Access Level: | Open access |
| Keyword: | aza-tryptophanes asymmetric synthesis chiral tridentate ligands Ni catalysis Tailor-Made Amino Acids (TM) Schiff bases dynamic kinetic resolution alpha-amino-acids ni(ii) complexes efficient synthesis drug discovery side-chains transamination inhibitors ligands analogs |
| Summary: | 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)-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. |
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