Synthesis of fluorinated donepezil by palladium-catalyzed decarboxylative allylation of alpha-fluoro-beta-keto ester with tri-substituted heterocyclic alkene and the self-disproportionation of its enantiomers

Maeno Mayaka; Kondo Hiroya; Tokunaga Etsuko; Shibata Norio

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Synthesis of fluorinated donepezil by palladium-catalyzed decarboxylative allylation of alpha-fluoro-beta-keto ester with tri-substituted heterocyclic alkene and the self-disproportionation of its enantiomers

机译：用三取代的杂环烯烃合成钯催化脱羧烯醇烯醇盐的氟化碳酸盐烯丙基烯丙基及其对映异构体的自歧化

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The synthesis of fluorinated donepezil, a promising new therapeutic agent for Alzheimer's disease, was achieved by the palladium-catalyzed decarboxylative allylation (DcA) of an allylic ester having a tri-substituted heterocyclic alkene system as a key step. This strategy is very different from a patented method for the title compound which was successfully extended to the first catalytic asymmetric synthesis of fluorinated donepezil. Fluorinated donepezil showed a noticeable magnitude in the self-disproportionation of enantiomers.

机译：通过将具有三取代的杂环烯烃系统的钯催化的脱羧烯丙基烯化（DCA）为关键步骤，通过具有三取代的杂环烯烃系统的钯催化的脱羧烯丙基烯化（DCA）来实现氟化胺基哌齐的新治疗剂。该策略与标题化合物的专利方法非常不同，该方法成功地延伸到氟化胺嘧啶的第一催化不对称合成。氟化硝基哌妥齐在对映体的自我抑制中显示出明显的幅度。

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来源
《RSC Advances》 |2016年第88期|共5页
作者
Maeno Mayaka; Kondo Hiroya; Tokunaga Etsuko; Shibata Norio;
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Nagoya Inst Technol Dept Nanopharmaceut Sci Showa Ku Nagoya Aichi 4668555 Japan;

Nagoya Inst Technol Dept Nanopharmaceut Sci Showa Ku Nagoya Aichi 4668555 Japan;

Nagoya Inst Technol Dept Nanopharmaceut Sci Showa Ku Nagoya Aichi 4668555 Japan;

Nagoya Inst Technol Dept Nanopharmaceut Sci Showa Ku Nagoya Aichi 4668555 Japan;

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正文语种 eng
中图分类化学;
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1. Synthesis of fluorinated donepezil by palladium-catalyzed decarboxylative allylation of alpha-fluoro-beta-keto ester with tri-substituted heterocyclic alkene and the self-disproportionation of its enantiomers [J] . Maeno Mayaka, Kondo Hiroya, Tokunaga Etsuko, RSC Advances . 2016,第88期

机译：用三取代的杂环烯烃合成钯催化脱羧烯醇烯醇盐的氟化碳酸盐烯丙基烯丙基及其对映异构体的自歧化
2. Enantioselective Palladium-Catalyzed Decarboxylative Allylation of -Keto Esters Assisted by a Thiourea [J] . Qian Hua, Gu Guoxian, Zhou Qinghai, Synlett . 2018,第1期

机译：硫脲辅助酯的映选择性钯催化的脱羧烯丙基酯
3. Easy access to esters with a benzylic quaternary carbon center from diallyl malonates by palladium-catalyzed decarboxylative allylation [J] . Imao D, Itoi A, Yamazaki A, The Journal of Organic Chemistry . 2007,第5期

机译：通过钯催化的脱羧烯丙基化反应，可容易地从丙二酸二烯丙酯中获得具有苄基季碳中心的酯
4. Palladium-Catalyzed Decarboxylative Benzylation of β-Keto Esters [C] . Kenta Ushijima, Ryoichi Kuwano Symposium on Organometallic Chemistry . 2007

机译：钯催化β-酮酯的脱羧苄基化
5. Palladium-catalyzed decarboxylative allylations of ester enolate equivalents and palladium-catalyzed cyclizations via CO2 and silyl activation. [D] . Ariyarathna, Yamuna. 2014

机译：钯催化的酯烯酸酯等效物的脱羧烯丙基化和钯催化的经由CO2和甲硅烷基活化的环化反应。
6. Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue via gravity-driven achiral chromatography: mechanistic rationale and implications [O] . Mayaka Maeno, Etsuko Tokunaga, Takeshi Yamamoto, 2015

机译：重力驱动非手性色谱法测定沙利度胺及其氟化类似物对映体的自歧化作用：机理和意义
7. Enantioselective Synthesis of Homoallylic Azides and Nitriles via Palladium-Catalyzed Decarboxylative Allylation [O] . Maria Victoria Vita, Paola Caramenti, Jerome Waser 2015

机译：通过钯催化脱羧烯丙基化致注重邻吡啶吡啶和腈的合成

Synthesis of fluorinated donepezil by palladium-catalyzed decarboxylative allylation of alpha-fluoro-beta-keto ester with tri-substituted heterocyclic alkene and the self-disproportionation of its enantiomers

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