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Efficient synthesis of precursors for cycloalkyne and cycloallene by rearrangement of silyl enol ether and isomerization of enolate

机译：基于甲硅烷基烯醇醚的重排和烯丙基异构的高效合成环炔和环烯的前体

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Strained cyclic compounds, such as cycloalkynes and cycloallenes, are reactive intermediates for the synthesis of multiply functionalized cyclic molecules.1 Among various precursors for these strained intermediates, α-silyl enol triflates have been most frequently utilized because the generation is promoted under the mild conditions;; however, preparation of these compounds requires four or five steps through protection and deprotection of the carbonyl group.2 In this study, we have developed one-pot synthesis of both precursors for cycloalkyne and cycloallene through rearrangement of silyl enol ethers and isomerization of lithium enolate.

机译：诸如环氧化物和环氧化物的应变环状化合物是用于合成乘法官能化环状分子的反应性中间体。对于这些应变中间体的各种前体，α-甲硅烷基烯醇三氟酯最常利用，因为在温和条件下促进了这一产生;;然而，这些化合物的制备需要通过羰基的保护和脱保护的四个或五个步骤.2在本研究中，我们通过重新排列甲硅烷基烯醇醚和烯醇锂的异构化了对环炔和环烯的一罐合成。。

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来源
《日本化学会春季年会講演予稿集》|2018年|1 CD-ROM|共1页
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Kazuki Inoue; Ryo Nakura; Kentaro Okano;
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正文语种
中图分类石油化学工业;
关键词
Cycloalkyne; Cycloallene; Highly Strained Intermediate; Rearrangement;

机译：cycloalkyne;Cycloallene;高度紧张的中间体;重新排列;

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1. ADDITION OF SILYL ENOL ETHERS AND SILYL KETENE ACETALS TO FERROCENYLMETHYL ETHERS - SYNTHESIS OF PRECURSORS TO CHIRAL BRIDGED FERROCENOPHANES [J] . Locke AJ., Richards CJ., Hibbs DE., Tetrahedron . 1996,第4期

机译：甲硅烷基醚和甲硅烷基乙炔醛向二甲乙炔基乙基醚的添加-手性桥联二苯醚的前体的合成
2. Synthesis of the hydroazulene portion of guanacastepene A using a [2.3]sigmatropic sulfoxide rearrangement: observations on silyl enol ether electrophilic chemistry for the introduction of the C-13 hydroxyl group [J] . Philip Magnus, Cyril Ollivier Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2002,第52期

机译：[2.3]σ亚砜重排合成胍基丁烯A的氢杂氮部分：甲硅烷基烯醇醚亲电化学对C-13羟基引入的观察
3. Synthesis of the hydroazulene portion of guanacastepene A using a [2.3]sigmatropic sulfoxide rearrangement: observations on silyl enol ether electrophilic chemistry for the introduction of the C-13 hydroxyl group [J] . Philip Magnus, Cyril Ollivier Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2002,第52期

机译：[2.3]σ亚砜重排合成胍基丁烯A的氢杂氮部分：甲硅烷基烯醇醚亲电化学对C-13羟基引入的观察
4. Efficient synthesis of precursors for cycloalkyne and cycloallene by rearrangement of silyl enol ether and isomerization of enolate [C] . Kazuki Inoue, Ryo Nakura, Kentaro Okano 日本化学会春季年会講演予稿集 . 2018

机译：基于甲硅烷基烯醇醚的重排和烯丙基异构的高效合成环炔和环烯的前体
5. The synthesis and reactivity of β-silyloxy silyl enol ethers, and, The total synthesis of Laurenditerpenol [D] . Im, G-Yoon 2007

机译：β-甲硅烷氧基甲硅烷基烯醇醚的合成与反应性，劳伦二萜醇的全合成
6. Facile isomerization of silyl enol ethers catalyzed by triflic imide and its application to one-pot isomerization–(2 + 2) cycloaddition [O] . Kazato Inanaga, Yu Ogawa, Yuuki Nagamoto, 2012

机译：三氟甲酰亚胺催化的甲硅烷基烯醇醚的轻松异构化及其在一锅异构化-（2 + 2）环加成中的应用
7. Convenient Synthesis of β-Silyl Ketones from β-Stannyl Enol Silyl Ethers via a 1,4 Anionic Rearrangement of Silicon [O] . Hiroyuki Nakahira, Ilhyong Ryu, Akiya Ogawa, 1990

机译：通过硅的1,4阴离子重排，方便地从β-甾烷基烯醇甲硅烷基醚中从β-甾烷基烯醇甲基甲硅烷基醚合成

Efficient synthesis of precursors for cycloalkyne and cycloallene by rearrangement of silyl enol ether and isomerization of enolate

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