Asymmetric synthesis of β-heterocycle substituted l-α-amino acids
| Autor: | V.S. Haroutunyan, Yu. N. Belokon, Satenik G. Petrosyan, A. S. Saghiyan, K. Fisher, Tariel V. Ghochikyan, Arpine V. Geolchanyan, A. A. Avetisyan |
|---|---|
| Rok vydání: | 2004 |
| Předmět: |
chemistry.chemical_classification
Schiff base Nucleophilic addition Chemistry Stereochemistry Organic Chemistry Enantioselective synthesis Decomposition Catalysis Amino acid Inorganic Chemistry chemistry.chemical_compound Dehydroalanine Stereoselectivity Physical and Theoretical Chemistry Enantiomer |
| Zdroj: | Tetrahedron: Asymmetry. 15:705-711 |
| ISSN: | 0957-4166 |
| DOI: | 10.1016/j.tetasy.2003.12.007 |
| Popis: | A new efficient method of asymmetric synthesis of β-heterocycle substituted l -α-amino acids through the addition of 3-amino-1,2,4-thiodiazole and 5-mercapto-1,2,4-triazoles, containing various substituents at the 3 and 4 positions, to the CC bond of dehydroalanine in the Ni(II) complex of its Schiff base with ( S )-2- N -( N ′ -benzylprolyl)aminobenzophenone has been elaborated upon. Under thermodynamic control, the stereoselectivity of the nucleophilic addition exceeded 94%. After acidic decomposition of the reaction mixtures, the corresponding β-heterocycle substituted α-amino acids with high enantiomeric purity (ee > 98.5%) were isolated. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect