Enantioselective Bifunctional Ammonium Salt‐Catalyzed Syntheses of 3‐CF3S‐, 3‐RS‐, and 3‐F‐Substituted Isoindolinones
| Autor: | Mario Waser, Andreas Eitzinger, Bernhard Spingler, Jan Otevrel, Antonio Massa, Antonio Macchia, Victoria Haider, Albrecht Berkessel, Kirill Faust |
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| Přispěvatelé: | University of Zurich, Waser, Mario |
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
10120 Department of Chemistry
Bifunctional catalysis 1503 Catalysis Heteroatom Salt (chemistry) 010402 general chemistry 01 natural sciences Update Catalysis Updates chemistry.chemical_compound 540 Chemistry Organic chemistry Ammonium Bifunctional chemistry.chemical_classification 010405 organic chemistry Organocatalysis Organofluorine chemistry Organic Chemistry Enantioselective synthesis General Chemistry 0104 chemical sciences Asymmetric phase-transfer catalysis chemistry Heterofunctionalization 1605 Organic Chemistry |
| Zdroj: | Advanced Synthesis & Catalysis |
| Popis: | We herein report the ammonium salt‐catalyzed synthesis of chiral 3,3‐disubstituted isoindolinones bearing a heteroatom functionality in the 3‐position. A broad variety of differently substituted CF3S‐ and RS‐derivatives were obtained with often high enantioselectivities when using Maruoka's bifunctional chiral ammonium salt catalyst. In addition, a first proof‐of‐concept for the racemic synthesis of the analogous F‐containing products was obtained as well, giving access to one of the rare examples of a fairly stable α‐F‐α‐amino acid derivative. |
| Databáze: | OpenAIRE |
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