Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates,Organic Letters

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Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates
Organic Letters ( IF 4.9 ) Pub Date : 2024-03-19 , DOI: 10.1021/acs.orglett.4c00818
David Svestka ₁ , Pavel Bobal ₁ , Mario Waser ₂ , Jan Otevrel ₁

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The piperidine-based Takemoto catalyst has been successfully employed in a novel asymmetric transfer hydroxymethylation of activated isoindolinones, allowing us to prepare the enantioenriched hydroxymethylated adducts in good to excellent yields (48–96%) and enantiopurities (81:19–97:3 e.r.). To increase the reaction rate without compromising the selectivity, carefully optimized formaldehyde surrogates were employed, providing a convenient source of anhydrous formaldehyde with a base-triggered release. The substrate scope, including 34 entries, showed the considerable generality of the asymmetric transformation, and most entries exhibited complete conversions in 24–48 h. A scale-up experiment and multiple enantioselective downstream transformations were also carried out, suggesting the prospective synthetic utility of the products.

中文翻译：

使用甲醛替代物进行异吲哚啉酮的不对称有机催化转移羟甲基化

基于哌啶的竹本催化剂已成功用于活化异吲哚啉酮的新型不对称转移羟甲基化，使我们能够以良好至优异的产率（48-96%）和对映体纯度（81:19-97:3 er）制备对映体富集的羟甲基化加合物。）。为了在不影响选择性的情况下提高反应速率，采用了仔细优化的甲醛替代物，提供了具有碱触发释放的无水甲醛的便捷来源。底物范围包括 34 个条目，显示了不对称转化的相当普遍性，大多数条目在 24-48 小时内表现出完全转化。还进行了放大实验和多个对映选择性下游转化，表明了产品的预期合成效用。

更新日期：2024-03-19

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