Function-oriented investigations of a peptide-based catalyst that mediates enantioselective allylic alcohol epoxidation
| Autor: | Nadia C. Abascal, Phillip A. Lichtor, Michael W. Giuliano, Scott J. Miller |
|---|---|
| Rok vydání: | 2014 |
| Předmět: |
Reaction conditions
chemistry.chemical_classification 010405 organic chemistry Chemistry Enantioselective synthesis Substrate (chemistry) Peptide General Chemistry Allylic alcohol 010402 general chemistry computer.software_genre 01 natural sciences Combinatorial chemistry Nmr data Article 0104 chemical sciences Catalysis Data mining computer Function (biology) |
| Zdroj: | Chem. Sci.. 5:4504-4511 |
| ISSN: | 2041-6539 2041-6520 |
| DOI: | 10.1039/c4sc01440e |
| Popis: | We detail an investigation of a peptide-based catalyst (6) that is effective for the site- (>100 : 1 : 1) and enantioselective epoxidation (86% ee) of farnesol. Studies of the substrate scope exhibited by the catalyst are included, along with an exploration of optimized reaction conditions. Mechanistic studies are reported, including relative rate determinations for the catalyst and propionic acid, a historical perspective, truncation studies, and modeling using NMR data. Our compiled data advances our understanding of the inner workings of a catalyst that was identified through combinatorial means. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|