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

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 spe...

Full description

Saved in:
Bibliographic Details
Published inACS omega Vol. 7; no. 30; pp. 26919 - 26927
Main Authors Corbisiero, Dario, Fantoni, Tommaso, Ferrazzano, Lucia, Martelli, Giulia, Cantelmi, Paolo, Mattellone, Alexia, Palladino, Chiara, Monari, Magda, Pedrazzani, Riccardo, Tolomelli, Alessandra, Cabri, Walter
Format Journal Article
LanguageEnglish
Published American Chemical Society 02.08.2022
Online AccessGet full text

Cover

More Information
Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.2c03477