Publications by authors named "Ido Domb"
Secondary-sphere modification in proline catalysis: old friend, new connection.
Chem Commun (Camb)
February 2022
In this work, we exploit our strategy of 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.
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- The study investigates how different solvents affect aldol reactions catalyzed by proline modified with boronic acids.
- It employs multivariate regression to analyze interactions between solvents, proline, and boronic acids, revealing the role of solvent-controlled microenvironments in reaction selectivity.
- The findings suggest that using chloroform as a solvent can optimize reaction conditions by reducing the amount of ketone needed while maintaining high yields and selectivity.