Asymmetric Synthesis of 3-Substituted Cyclohexylamine Derivatives from Prochiral DiketonesviaThree Biocatalytic Steps
| Autor: | Gideon Grogan, Walter M. F. Fabian, Barbara Grischek, Elina Siirola, Wolfgang Kroutil, Francesco G. Mutti, Sebastian F. Hoefler |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2013 |
| Předmět: |
biology
Bicyclic molecule 010405 organic chemistry Chemistry Diastereomer Enantioselective synthesis Substrate (chemistry) General Chemistry Cyclohexylamine 010402 general chemistry 01 natural sciences 0104 chemical sciences chemistry.chemical_compound Hydrolysis Hydrolase biology.protein Organic chemistry Lipase |
| Zdroj: | Advanced Synthesis & Catalysis |
| ISSN: | 1615-4150 |
| DOI: | 10.1002/adsc.201201057 |
| Popis: | Prochiral bicyclic diketones were transformed to a single diastereomer of 3-substituted cyclohexylamine derivatives via three consecutive biocatalytic steps. The two chiral centres were set up by a CC hydrolase (6-oxocamphor hydrolase) in the first step and by an ω-transaminase in the last step. The esterification of the intermediate keto acid was catalysed by a lipase in the second step if possible. For two substrates the CC hydrolytic step as well as the esterification could be run simultaneously in a one-pot cascade in an organic solvent. In one example, the reaction mixture of the first two steps could be directly subjected to bio-amination in an organic solvent without the need to change the reaction medium. Depending on the choice of the ω-transaminase employed and the substrate the cis- as well as the trans-diastereomers could be obtained in optically pure forms. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
| Nepřihlášeným uživatelům se plný text nezobrazuje | K zobrazení výsledku je třeba se přihlásit. |