Regioselective catalytic asymmetric N-alkylation of isoxazol-5-ones with para-quinone methides

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 isoxazolinone...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2020-04, Vol.18 (13), p.2398-2404
Main Authors: Qi, Suo-Suo, Jiang, Zhen-Hui, Chu, Ming-Ming, Wang, Yi-Feng, Chen, Xue-Yang, Ju, Wan-Zhen, Xu, Dan-Qian
Format: Article
Language:English
Subjects:
Alkylation
Asymmetry
Catalysts
Crystallography
Enantiomers
Nucleophiles
Quinones
Regioselectivity
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob00393j