Direct Synthesis of alpha-Allenols from TMS-Protected Alkynes and Aldehydes Mediated by Tetrabutylammonium Fluoride

Huang Xiaojun; Bugarin Alejandro

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Direct Synthesis of alpha-Allenols from TMS-Protected Alkynes and Aldehydes Mediated by Tetrabutylammonium Fluoride

机译：由四丁基氟化铵介导的TMS保护的炔烃和醛直接合成α-烯丙醇

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A unique chemoselective synthesis of alpha-allenic alcohols is presented. Tetrabutylammonium fluoride (TBAF) mediated this transformation under mild reaction conditions. A range of functional groups is well-tolerated in this reaction, while affording adducts in moderate to excellent yields (48-96%, average 76 %). Mechanistic studies, including the use of tetrabutylammonium hydroxide (TBAH), revealed that the hydroxide ion can be the responsible for the observed rearrangement.

机译：提出了独特的α-烯烃醇的化学选择性合成。四丁基氟化铵（TBAF）在温和的反应条件下介导了这种转化。在该反应中，一系列官能团具有良好的耐受性，同时以中等至极好的收率（48-96％，平均76％）提供加合物。包括使用四丁基氢氧化铵（TBAH）在内的机械研究表明，氢氧根离子可能是所观察到的重排的原因。

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《Chemistry: A European journal》 |2016年第36期|共5页
作者
Huang Xiaojun; Bugarin Alejandro;
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正文语种 eng
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aldehydes; heterocycles; tetrabutylammonium fluoride; TMS-protected alkynes; alpha-allenols;

机译：醛;杂环;四丁基氟化铵;TMS保护的炔烃;α-烯醇;

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1. Direct Synthesis of alpha-Allenols from TMS-Protected Alkynes and Aldehydes Mediated by Tetrabutylammonium Fluoride [J] . Huang Xiaojun, Bugarin Alejandro Chemistry: A European journal . 2016,第36期

机译：由四丁基氟化铵介导的TMS保护的炔烃和醛直接合成α-烯丙醇
2. Direct Vinylogous Aldol Reaction Triggered by Tetrabutylammonium Fluoride: A Highly Regioselective and Diastereoselective Addition of Cyclic β-Haloenals to Aromatic Aldehydes [J] . Jingli Zhang, Lianghu Gu, Yuefa Gong Synlett . 2012,第3期

机译：四丁基氟化铵引发的直接乙烯基醛醇缩合反应：环β-卤代醛对芳族醛的高度区域选择性和非对映选择性加成。
3. Synthesis of Alkynes from Vinyl Triflates Using Tetrabutylammonium Fluoride [J] . Okutani Masaru, Mori Yuji Chemical and Pharmaceutical Bulletin . 2015,第5期

机译：四丁基氟化铵由乙烯基三氟甲磺酸酯合成炔烃
4. Methoxylation of Aroyl Fluorides with Cyclopentyl Methyl Ether Mediated by Tetrabutylammonium difluorotriphenylsilicate (TBAT) [C] . Zhenhua Wang, Xiu Wang, Yasushi Nishihara 日本化学会春季年会講演予稿集 . 2018

机译：用四氟甲基二苯基硅基硅酸酯介导的环戊基甲基醚的芳酰氟化物（TBAT）
5. Part I. Asymmetric organocatalysis: (1) Direct enantioselective organocatalytic hydroxymethylation of aldehydes catalyzed by alpha,alpha-diphenylprolinol trimethylsilyl ether: Application in the formal synthesis of (-)-Rasfonin; (2) Synthesis of a novel bicyclic secondary amine organocatalyst: Application to the direct enantioselective organocatalytic hydroxymethylation of aldehydes. Part II. Asymmetric synthesis of bicyclic analogues of the anti-osteoporotic drug risedronate. [D] . Miller, John Robert. 2010

机译：第一部分，不对称有机催化：（1）α，α-二苯基脯氨醇三甲基甲硅烷基醚催化的醛的直接对映选择性有机催化羟甲基化：在（-）-Rasfonin的正式合成中的应用；（2）新型双环仲胺有机催化剂的合成：应用于醛的直接对映选择性有机催化羟甲基化。第二部分抗骨质疏松药物Risedronate的双环类似物的不对称合成。
6. Alkyne Cycloadditions Mediated by Tetrabutylammonium Fluoride: A Unified and Diversifiable Route to Isoxazolines and Pyrazolines [O] . Edith Nagy, Salvatore D. Lepore -1

机译：四丁基氟化铵介导的炔烃环加成反应：异恶唑啉和吡唑啉的统一且可分散的路线
7. Direct Synthesis of α‐Allenols from TMS‐Protected Alkynes and Aldehydes Mediated by Tetrabutylammonium Fluoride [O] . Xiaojun Huang, Alejandro Bugarin 2016

机译：直接合成来自四丁基氟化铵介导的TMS保护的炔烃和醛的α-甲苯烯酚

Direct Synthesis of alpha-Allenols from TMS-Protected Alkynes and Aldehydes Mediated by Tetrabutylammonium Fluoride

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