Regioselective catalytic asymmetric <i>N</i>-alkylation of isoxazol-5-ones with <i>para</i>-quinone methides
Suo‐Suo Qi, Zhen-Hui Jiang, Mingming Chu, Yi-Feng Wang, Xueyang Chen, Wan-Zhen Ju, Dan‐Qian Xu
Abstract
A highly regioselective and enantioselective N-alkylation of isoxazol-5-ones with para-quinone methides promoted by bi-functional squaramide catalysts was developed. This unexpected asymmetric N-addition of isoxazolinones afforded a series of enantioenriched N-diarylmethane substituted isoxazolinones with high yields and enantioselectivities (up to 97 : 3 er). This reaction not only provides a useful approach for intermolecular chiral C-N bond formation but also demonstrates the immense potential of isoxazol-5-ones as N-nucleophiles in catalytic asymmetric reactions.
Topics & Concepts
ChemistryRegioselectivityAlkylationCatalysisQuinoneCombinatorial chemistryMedicinal chemistryOrganic chemistryStereochemistrySynthesis of Indole DerivativesChemical Synthesis and ReactionsAxial and Atropisomeric Chirality Synthesis