Asymmetric 1,6-Conjugate Addition of para-Quinone Methides for the Synthesis of Chiral β,β-Diaryl-α-Hydroxy Ketones,Advanced Synthesis & Catalysis

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Asymmetric 1,6-Conjugate Addition of para-Quinone Methides for the Synthesis of Chiral β,β-Diaryl-α-Hydroxy Ketones
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2017-11-15 05:30:58 , DOI: 10.1002/adsc.201700947
Yuan-Yuan Gao ₁ , Yuan-Zhao Hua ₁ , Min-Can Wang ₁

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A direct asymmetric 1,6-conjugated addition of α-hydroxy ketone to para-quinone methides has been developed. It is an efficient approach to the synthesis of chiral β,β-diaryl-α-hydroxy ketones. The reaction runs smoothly in the presence of ZnEt₂ and nonracemic bis(diarylhydroxymethylpyrrolidinylmethyl)phenols (ProPhenols), and the desired products are obtained in good yields (up to 88%) and with high stereoselectivity (up to >99% ee and up to >99:1 dr). This reaction also can be run on a gram scale without impacting its enantioselectivity.

中文翻译：

对苯二甲腈的不对称1,6-共轭加成反应合成手性β，β-二芳基-α-羟基酮

已经开发了α-羟基酮直接不对称的1，6-共轭加成到对醌甲基化物中。这是合成手性β，β-二芳基-α-羟基酮的有效方法。该反应在ZnEt ₂和非外消旋双（二芳基羟甲基吡咯烷二甲基甲基）苯酚（ProPhenols）的存在下顺利进行，并以良好的收率（最高88％）和高的立体选择性（最高ee> 99％和最高ee）获得了所需的产物。 > 99：1博士）。该反应也可以以克规模进行，而不会影响其对映选择性。

更新日期：2017-11-16

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