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

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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.

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

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Article information


Submitted
22 Feb 2020
Accepted
13 Mar 2020
First published
14 Mar 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Communication

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

S. Qi, Z. Jiang, M. Chu, Y. Wang, X. Chen, W. Ju and D. Xu, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB00393J

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