Organocatalytic Desymmetrisation of Fittig’s Lactones: Deuterium as a Reporter Tag for Hidden Racemisation
| Autor: | Máté Berta, Péter Spránitz, Tibor Soós, Petra Sőregi, Bence Béla Botlik |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
biology
010405 organic chemistry Aryl Organic Chemistry Enantioselective synthesis Cinchona Glutaric acid 010402 general chemistry biology.organism_classification 01 natural sciences Desymmetrization Catalysis 0104 chemical sciences Stereocenter chemistry.chemical_compound chemistry Organic chemistry Bifunctional Racemization |
| Zdroj: | Synthesis. 51:1263-1272 |
| ISSN: | 1437-210X 0039-7881 |
| Popis: | Highly enantioselective desymmetrisation of Fittig’s lactones with alcohols is promoted by bifunctional cinchona squaramides. The reactions were carried out with monodeuterated methanol to detect possible hidden racemisation of the stereogenic centre. Current evidence suggests that racemisation was not a relevant process for most substrates; partial erosion of enantioselectivity was only detected with ortho-substituted aryl derivates. The resultant glutaric acid derivatives possess a scaffold that is common in natural products and the compounds are also useful chiral building blocks for further synthetic endeavours. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|