Dienolate‐Mediated, Regioselective C2‐Polarity Reversal of Chromone‐Based Reactants and Their Application in Nucleophilic Strategies,Advanced Synthesis & Catalysis

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Dienolate‐Mediated, Regioselective C2‐Polarity Reversal of Chromone‐Based Reactants and Their Application in Nucleophilic Strategies
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-09-24 , DOI: 10.1002/adsc.202000942
Zhen Yao ₁ , Xiong-Wei Liu ₂ , Zheng Li ₁ , Sheng-Wen Xu ₁ , Lijin Xu ₃ , Xiong-Li Liu ₁

Affiliation

Inspired by the chemistry and biology of chromone, a method for the construction of spirooxindole‐based tetrahydrocyclopenta[b]chromanones is reported with good regio‐ and diastereoselectivity (all cases >20:1 dr) and moderate yields (up to 67%). This method leads to the construction of four contiguous stereogenic tertiary centers and one spiro quaternary center via a one‐step γ‐regioselective cascade [3+2] cycloaddition of an oxindole‐chromone synthon with 3‐methyl‐4‐nitro‐5‐alkenyl‐isoxazole.

中文翻译：

苯甲酸酯基反应物的二烯酸酯介导的区域选择性C2极性逆转及其在亲核策略中的应用

受色酮化学和生物学的启发，据报道，一种基于螺氧杂吲哚的四氢环戊四烯[ b ]色酮的构建方法具有良好的区域选择性和非对映选择性（所有情况> 20：1 dr）和中等产率（最高67％）。该方法通过一个羟吲哚-色酮合成子与3-甲基-4-4-硝基-5-烯基的一步式γ-区域选择性级联[3 + 2]环加成反应，从而构建了四个连续的立体成因三级中心和一个螺旋四级中心。异唑

更新日期：2020-09-24

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