Asymmetric Double Oxidative [3 + 2] Cycloaddition for the Synthesis of CF3-Containing Spiro[pyrrolidin-3,2′-oxindole],Organic Letters

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Asymmetric Double Oxidative [3 + 2] Cycloaddition for the Synthesis of CF3-Containing Spiro[pyrrolidin-3,2′-oxindole]
Organic Letters ( IF 4.9 ) Pub Date : 2023-04-21 , DOI: 10.1021/acs.orglett.3c01083
Tao Wang ₁ , Wen-Bin Wang ₁ , Yan-Ming Fu ₁ , Cheng-Feng Zhu ₁ , Lan-Jun Cheng ₁ , Yang-En You ₁ , Xiang Wu ₁ , You-Gui Li ₁

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An asymmetric double oxidative [3 + 2] cycloaddition is reported. Oxidation of 3-((2,2,2-trifluoroethyl)amino)indolin-2-ones and β-aryl-substituted aldehydes simultaneously and subsequent asymmetric cycloaddition in the presence of the chiral amino catalyst generated highly functionalized chiral CF₃-containing spiro[pyrrolidin-3,2′-oxindole] with four contiguous stereocenters stereoselectively, which is characterized by directly constructing two C–C bonds from four C(sp³)–H bonds. This new method features mild conditions, broad substrate scope, and excellent functional group compatibility.

中文翻译：

不对称双氧化 [3 + 2] 环加成法合成含 CF3 的螺[pyrrolidin-3,2'-oxindole]

报道了不对称双氧化 [3 + 2] 环加成。在手性氨基催化剂存在下，同时氧化 3-((2,2,2-trifluoroethyl)amino)indolin-2-ones 和 β-aryl-substitutional aldehydes 以及随后的不对称环加成生成高度官能化的手性 CF 3_螺环[pyrrolidin-3,2'-oxindole] 具有四个连续的立构中心立体选择性，其特征在于由四个 C(sp ³ )–H 键直接构建两个 C–C 键。这种新方法具有条件温和、底物适用范围广、官能团相容性好等特点。

更新日期：2023-04-21

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