| Autor: |
Domb I; Department of Chemistry, Ben-Gurion University of the Negev, Beer Sheva, Israel. anatmilo@bgu.ac.il., Lustosa DM; Department of Chemistry, Ben-Gurion University of the Negev, Beer Sheva, Israel. anatmilo@bgu.ac.il., Milo A; Department of Chemistry, Ben-Gurion University of the Negev, Beer Sheva, Israel. anatmilo@bgu.ac.il. |
| Jazyk: |
angličtina |
| Zdroj: |
Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2022 Feb 08; Vol. 58 (12), pp. 1950-1953. Date of Electronic Publication: 2022 Feb 08. |
| DOI: |
10.1039/d1cc05589e |
| Abstrakt: |
In this work, we exploit our strategy of in situ secondary-sphere modification of organocatalysts to improve the reactivity and selectivity of amino catalysts. Herein, the carboxylic acid moiety of proline was targeted as a site for modification under catalytic reaction conditions with boronic acids. Intermolecular aldol reactions between aromatic aldehydes and cyclopentanone were selected as a proof-of-concept because cyclopentanone as an aldol donor was often associated with decreased selectivity compared to its 6-membered ring analog, hexanone. Our secondary-sphere modification strategy, using naturally occurring L-proline amino acid, enabled reactions at room temperature with high levels of diastereo- and enantio-selectivity and short reaction times. NMR and HR-MS studies shed light on the nature of the catalyst structure and on the role of water in our reactions. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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