Catalyst-free selenylation/semipinacol rearrangement cascades of alkenyl cyclobutanols: synthesis of β-selenylated cyclopentanones

Dae Young Kim

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Catalyst-free selenylation/semipinacol rearrangement cascades of alkenyl cyclobutanols: synthesis of β-selenylated cyclopentanones

机译：无催化剂 - 无苯烯醇化/半碱醇重排级联链烯基环丁醇：合成β-硒化环戊酮

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A simple and practical strategy to access b-selenated cyclic ketone derivatives through the catalyst-free selenylation and semipinacol rearrangement sequence of 1-(1-arylvinyl)cyclobutanols was developed. This reaction employs the easily accessible and shelf-stable benzeneselenyl bromide as an electrophilic selenium source, and the reaction has advantages of mild reaction conditions and broad substrate scope.

机译：开发了通过催化剂 - 无苯乙烯化和半吡啶醇重排序列的简单实际的策略，并开发了1-（1-芳基乙烯基）环丁醇的半丙烯酸和半藻醇重排序列。该反应采用易于进入和货架稳定的苯二烯基溴作为电泳硒源，反应具有温和的反应条件温和的优点和宽的基材范围。

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来源
《Synthetic Communications》 |2019年第20期|共7页
作者
Dae Young Kim;
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作者单位

Department of Chemistry Soonchunhyang University Asan Republic of Korea;

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原文格式 PDF
正文语种 eng
中图分类有机化学;
关键词
1; 2-Alkyl migration; 1-(1-arylvinyl)cyclobutanols; benzeneselenyl bromide; selenylation; semipinacol rearrangement;

机译：1;2-烷基迁移;1-（1-芳基乙烯基）环丁醇;苯磺酸苯溴化物;亚苯基化;半素醇重新排列;

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专利

1. Catalyst-free selenylation/semipinacol rearrangement cascades of alkenyl cyclobutanols: synthesis of β-selenylated cyclopentanones [J] . Dae Young Kim Synthetic Communications . 2019,第17a20期

机译：无催化剂 - 无苯烯醇化/半碱醇重排级联链烯基环丁醇：合成β-硒化环戊酮
2. Copper‐promoted Synthesis of β‐Selenylated Cyclopentanones via Selenylation and 1,2‐Alkyl Migration Sequences of Alkenyl Cyclobutanols [J] . Yubin Kim, Dae Young Kim Bulletin of the Korean Chemical Society . 2020,第3期

机译：通过硒化酶化和烯基环丁醇的1,2-烷基迁移序列促进β-硒化环戊酮的合成
3. Copper-promoted Synthesis of P-Selenylated Cyclopentanones via Selenylation and 1,2-Alkyl Migration Sequences of Alkenyl Cyclobutanols [J] . Bulletin of the Korean Chemical Society . 2020,第3期

机译：通过硒化酶化和烯基环丁醇的1,2-烷基迁移序列促进铜促进合成p-硒化环戊酮
4. Part I: Chloronium-induced semipinacol rearrangement for the construction of the tetracyclic core of acutumine and progress toward a total synthesis of acutumine Part II: Progress toward a total synthesis of paecilomycine A [D] . Bittner, Amy Rebecca 2012

机译：第一部分：氯诱导的半松果酚重排用于金刚烷四环核心的构建，并向全合成金刚霉素进展第二部分：向全合成青霉素A的进展
5. Carbamoyl Radical-Mediated Synthesis and Semipinacol Rearrangement of β-Lactam Diols [O] . Marie Betou, Louise Male, Jonathan W Steed, -1

机译：氨基甲酰基自由基介导的β-内酰胺二醇的合成和半松果酚重排
6. Synthesis of Macrocyclic Ketones through Catalyst-Free Electrophilic Halogen-Mediated Semipinacol Rearrangement: Application to the Total Synthesis of ()-Muscone [O] . -1

机译：通过无催化剂的亲电卤素介导的半碱重新排列合成大环酮：在（）-MUSCONE的总合成中的应用

Catalyst-free selenylation/semipinacol rearrangement cascades of alkenyl cyclobutanols: synthesis of β-selenylated cyclopentanones

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