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.

Fast MacMillan's Imidazolidinone-Catalyzed Enantioselective Synthesis of Polyfunctionalized 4-Isoxazoline Scaffolds / Dario Corbisiero, Tommaso Fantoni, Lucia Ferrazzano, Giulia Martelli, Paolo Cantelmi, Alexia Mattellone, Chiara Palladino, Magda Monari, Riccardo Pedrazzani, Alessandra Tolomelli, Walter Cabri. - In: ACS OMEGA. - ISSN 2470-1343. - STAMPA. - 7:30(2022), pp. 3477.26919-3477.26927. [10.1021/acsomega.2c03477]

Fast MacMillan's Imidazolidinone-Catalyzed Enantioselective Synthesis of Polyfunctionalized 4-Isoxazoline Scaffolds

Dario Corbisiero
Primo
Investigation
;
Tommaso Fantoni
Investigation
;
Lucia Ferrazzano
Secondo
Conceptualization
;
Giulia Martelli
Visualization
;
Paolo Cantelmi
Writing – Review & Editing
;
Alexia Mattellone
Investigation
;
Chiara Palladino
Investigation
;
Magda Monari
Methodology
;
Riccardo Pedrazzani
Investigation
;
Alessandra Tolomelli
Penultimo
Conceptualization
;
Walter Cabri
Ultimo
Conceptualization
2022

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.
2022
Fast MacMillan's Imidazolidinone-Catalyzed Enantioselective Synthesis of Polyfunctionalized 4-Isoxazoline Scaffolds / Dario Corbisiero, Tommaso Fantoni, Lucia Ferrazzano, Giulia Martelli, Paolo Cantelmi, Alexia Mattellone, Chiara Palladino, Magda Monari, Riccardo Pedrazzani, Alessandra Tolomelli, Walter Cabri. - In: ACS OMEGA. - ISSN 2470-1343. - STAMPA. - 7:30(2022), pp. 3477.26919-3477.26927. [10.1021/acsomega.2c03477]
Dario Corbisiero, Tommaso Fantoni, Lucia Ferrazzano, Giulia Martelli, Paolo Cantelmi, Alexia Mattellone, Chiara Palladino, Magda Monari, Riccardo Pedrazzani, Alessandra Tolomelli, Walter Cabri
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/899503
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