1. Fast MacMillan’s Imidazolidinone-Catalyzed Enantioselective Synthesis of Polyfunctionalized 4-Isoxazoline Scaffolds
- Author
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Dario Corbisiero, Tommaso Fantoni, Lucia Ferrazzano, Giulia Martelli, Paolo Cantelmi, Alexia Mattellone, Chiara Palladino, Magda Monari, Riccardo Pedrazzani, Alessandra Tolomelli, Walter Cabri, and Dario Corbisiero, Tommaso Fantoni, Lucia Ferrazzano, Giulia Martelli, Paolo Cantelmi, Alexia Mattellone, Chiara Palladino, Magda Monari, Riccardo Pedrazzani, Alessandra Tolomelli, Walter Cabri
- Subjects
General Chemical Engineering ,General Chemistry ,ASYMMETRIC ORGANOCATALYSIS ORGANIC CATALYSIS NITRONES STRATEGIES DESIGN AMINE - Abstract
The enantioselective 1,3-dipolar cycloaddition of nitrones and arylpropionaldehydes to generate highly functionalized scaffolds for application in drug discovery was herein investigated. The use of a second-generation MacMillan catalyst as hydrochloride salt consistently accelerated the reaction speed, allowing a decrease in the reaction time up to >100 times, still affording 4-isoxazolines with good to excellent enantiomeric ratios at room temperature. As a proof of concept, further functionalization of the isoxazoline core through Pd-catalyzed cross-coupling was performed, generating differently functionalized chemical architectures in high yield.
- Published
- 2022
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