Chiral-boron-Lewis-acid-catalysed desymmetric ring expansion of 4-substituted cyclohexanones with α-diazomethylphosphonates,Organic Chemistry Frontiers

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Chiral-boron-Lewis-acid-catalysed desymmetric ring expansion of 4-substituted cyclohexanones with α-diazomethylphosphonates
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2023-02-13 , DOI: 10.1039/d2qo01912d
Xiaofeng Li ₁ , Pingping He ₁ , Peng Zhu ₁ , Yinhong Tang ₁ , Yungui Peng ₁

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A method for desymmetrizing asymmetric ring expansion of 4-substituted cyclohexanones with α-diazomethylphosphonates catalyzed by a chiral boron Lewis acid has been developed. The method affords β-ketophosphonate compounds bearing a stereogenic center at the α-position in up to 80% yields, 86% ee, and >20 : 1 dr. The obtained products can be further derivatized, demonstrating the synthetic potential of this reaction.

中文翻译：

手性硼路易斯酸催化 4-取代环己酮与 α-重氮甲基膦酸酯的不对称扩环

开发了一种通过手性硼路易斯酸催化的 α-重氮甲基膦酸酯使 4-取代环己酮的不对称扩环去对称化的方法。该方法以高达 80% 的产率、86% ee 和 >20 : 1 dr 提供在 α 位带有立体异构中心的 β-酮膦酸酯化合物。所得产物可以进一步衍生化，证明了该反应的合成潜力。

更新日期：2023-02-13

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