Organocatalytic Biomimetic Decarboxylative Aldol Reaction of Fluorinated β‐Keto Acids with Unprotected Isatins,Advanced Synthesis & Catalysis

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Organocatalytic Biomimetic Decarboxylative Aldol Reaction of Fluorinated β‐Keto Acids with Unprotected Isatins
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2018-09-04 , DOI: 10.1002/adsc.201800831
Yin‐Long Li _{1,

2} , Xue‐Lin Wang ₂ , Dan Xiao ₁ , Ming‐Ying Liu ₁ , Yunfei Du ₂ , Jun Deng _{1,

2}

Affiliation

A facile asymmetric synthesis of fluorinated 3‐hydroxyoxindoles through the biomimetic decarboxylative aldol reaction of fluorinated β‐keto acids with unprotected isatins catalyzed by quinine‐derived urea catalyst has been achieved. One of the features of this work is that the easily available α, α‐difluoro/α‐monofluoro‐β‐keto acids have been first applied in the enantioselective synthesis of fluorinated compounds as the masked fluoroenolates. Furthermore, the utility of this method was demonstrated by its ability to access a series of difluorinated 3‐hydroxyoxindoles with up to 95% ee and monofluorinated 3‐hydroxyoxindoles with up to 90 : 10 d.r. and 94% ee.

中文翻译：

氟代β-酮酸与未经保护的靛红的有机催化仿生脱羧羟醛反应

通过奎宁衍生的尿素催化剂催化氟化β-酮酸与未保护的靛红类素的仿生脱羧醛醇缩合反应，可以轻松实现氟化3-羟基羟吲哚的不对称合成。这项工作的特点之一是，容易获得的α，α-二氟/α-单氟-β-酮酸已首先用于作为掩蔽的氟烯酸酯的氟化化合物的对映选择性合成。此外，该方法的实用性还可以通过它访问一系列具有高达95％ee的二氟化3-羟基羟吲哚和具有高达90:10 dr和94％ee的单氟化3-羟基羟吲哚的能力得到证明。

更新日期：2018-09-04

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