Regioselective catalytic asymmetric N-alkylation of isoxazol-5-ones with para-quinone methides,Organic & Biomolecular Chemistry

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Regioselective catalytic asymmetric N-alkylation of isoxazol-5-ones with para-quinone methides
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2020/03/14 , DOI: 10.1039/d0ob00393j
Suo-Suo Qi _{1,

2,

3,

4,

5} , Zhen-Hui Jiang _{1,

2,

3,

4,

5} , Ming-Ming Chu _{1,

2,

3,

4,

5} , Yi-Feng Wang _{1,

2,

3,

4,

5} , Xue-Yang Chen _{1,

2,

3,

4,

5} , Wan-Zhen Ju _{1,

2,

3,

4,

5} , Dan-Qian Xu _{1,

2,

3,

4,

5}

Affiliation

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.

中文翻译：

异恶唑-5-酮与对醌甲基的区域选择性催化不对称N-烷基化

发展了由双功能方酰胺催化剂促进的对恶唑-5-酮与对醌甲基化物的高度区域选择性和对映选择性的N-烷基化。异恶唑啉酮的这种意想不到的不对称N-加成，提供了一系列高产率和对映选择性（高达97：3 er）的对映体富集的N-二芳基甲烷取代的异恶唑啉酮。该反应不仅为分子间手性C–N键的形成提供了一种有用的方法，而且证明了异恶唑-5-酮作为N-亲核试剂在催化不对称反应中的巨大潜力。

更新日期：2020-04-01

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