State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Key Laboratory of Green Pesticides and Cleaner Production Technology of Zhejiang Province, Department of Green Chemistry and Technology, Zhejiang University of Technology, Hangzhou 310014, P. R. China.
Org Biomol Chem. 2020 Apr 1;18(13):2398-2404. doi: 10.1039/d0ob00393j.
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.
双功能螺二酰胺催化剂促进的异噁唑-5-酮与对醌甲川的高区域和对映选择性 N-烷基化反应得到了发展。这种异噁唑啉酮的意外不对称 N-加成反应以高产率和对映选择性（高达 97:3 er）提供了一系列对映富集的 N-二芳基甲烷取代的异噁唑啉酮。该反应不仅为分子间手性 C-N 键形成提供了一种有用的方法，而且还展示了异噁唑-5-酮作为催化不对称反应中 N-亲核试剂的巨大潜力。
