Enantioselective protonation of monofluorinated silyl enol ethers by cooperative cation-binding catalysis,Bulletin of the Korean Chemical Society

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Enantioselective protonation of monofluorinated silyl enol ethers by cooperative cation-binding catalysis
Bulletin of the Korean Chemical Society ( IF 2.3 ) Pub Date : 2023-01-16 , DOI: 10.1002/bkcs.12675
Min‐Jung Jung ₁ , Sushovan Paladhi _{1,

2} , Choong Eui Song ₁

Affiliation

Herein, we report on the successful enantioselective protonation of a range of silyl enol ethers of cyclic ketones with labile chiral secondary CF bonds by using Song's chiral oligoethylene glycols (oligoEGs) as cation-binding catalysts in the presence of CsF and a proton source. Highly enantioselective protonations of an array of silyl enol ethers of α-fluoro tetralones and α-fluoro benzosuberones were achieved, producing corresponding chiral α-secondary α-fluoro cyclic ketones in full conversion, with up to 96% ee. Furthermore, this protocol has successfully been extended to access chiral α-choro and α-bromo cyclic ketones. This successful in situ generated fluoride ion-based stereoselective catalysis was driven by creating a densely confined chiral cage from the chiral catalyst, substrate, and CsF.

中文翻译：

协同阳离子结合催化单氟化甲硅烷基烯醇醚的对映选择性质子化

在此，我们报道了在 CsF 和质子源存在下，通过使用 Song 的手性低聚乙二醇 (oligoEG) 作为阳离子结合催化剂，一系列具有不稳定手性二级 C  F 键的环酮甲硅烷基烯醇醚成功对映选择性质子化. 实现了一系列 α-氟四氢萘酮和 α-氟苯并环酮的甲硅烷基烯醇醚的高对映选择性质子化，产生相应的手性 α-仲 α-氟环酮，完全转化，ee 高达 96%。此外，该协议已成功扩展到访问手性 α-choro 和 α-溴环酮。这种成功的原位生成的基于氟离子的立体选择性催化是通过从手性催化剂、底物和 CsF 中创建一个密集限制的手性笼来驱动的。

更新日期：2023-01-16

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