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Enantioselective Fluorination of α-Branched β-Ynone Esters Using a Cinchona-Based Phase-Transfer Catalyst.
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2020-09-21 , DOI: 10.1021/acs.joc.0c01997
Satoru Arimitsu 1 , Satsuki Iwasa 1 , Ryunosuke Arakaki 1
Affiliation  

Herein, we report the fluorination of α-branched β-ynone esters to afford their corresponding quaternary fluorinated products with good enantioselectivity (ee = 73–90%) using a cinchona-based phase-transfer catalyst. α-Branched β-ynone esters possess a highly acidic α-proton and form their corresponding enolate as a single isomer, which allows the enantioselective fluorination reaction to occur under standard cinchona-based phase-transfer catalyst conditions. Moreover, the obtained α-fluorinated product can be treated with [(SPhos)AuNTf2] (1 mol %) to afford a fluorinated 3,5-diketo carboxylic acid.

中文翻译:

使用基于金鸡纳的相转移催化剂对α-支化的β-Yone酯进行对映选择性氟化。

在本文中,我们报告了使用金鸡纳基相转移催化剂对α-支链β-炔酮进行氟化,以提供具有良好对映选择性(ee = 73-90%)的相应的季氟化产物。α-支化的β-炔酮酯具有高酸性的α-质子,并以单个异构体的形式形成其相应的烯醇化物,这使得对映选择性的氟化反应可以在基于金鸡纳纳的标准相转移催化剂条件下发生。此外,所得的α-氟化产物可用[(SPhos)AuNTf 2 ](1mol%)处理,得到氟化的3,5-二酮羧酸。
更新日期:2020-10-02
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