Synthesis of gamma-Boryl-Substituted Homoallylic Alcohols with anti Stereochemistry Based on a Double-Bond Transposition

Miura Tomoya; Nakahashi Junki; Sasatsu Takanori; Murakami Masahiro

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Synthesis of gamma-Boryl-Substituted Homoallylic Alcohols with anti Stereochemistry Based on a Double-Bond Transposition

机译：基于双键输液的抗立体化学合成γ-硼酸γ取代的主体醇

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摘要

The stereoselective synthesis of anti isomers of gamma-boryl-substituted homoallylic alcohols is disclosed. (E)-1,2-Di(boryl)alk-1-enes undergo Ru-catalyzed double-bond transposition with control of the geometry. The in situ generated (E)-1,2-di(boryl)alk-2-enes add to aldehydes in a stereospecific manner. The alkenylboron group within the product is amenable to a variety of synthetic derivatizations.

机译：公开了γ-硼酸γ-取代的主体醇抗异构体的立体选择性合成。（e）-1,2-Di（硼）Alk-1- ene经历Ru催化的双键转子，对几何形状进行控制。原位生成（e）-1,2-Di（硼）Alk-2-Enes以立体化的方式加入醛。产物中的链烯酰基组适用于各种合成衍生化。

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来源
《Angewandte Chemie》 |2019年第4期|共5页
作者
Miura Tomoya; Nakahashi Junki; Sasatsu Takanori; Murakami Masahiro;
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作者单位

Kyoto Univ Dept Synthet Chem &

Biol Chem Kyoto 6158510 Japan;

Kyoto Univ Dept Synthet Chem &

Biol Chem Kyoto 6158510 Japan;

Kyoto Univ Dept Synthet Chem &

Biol Chem Kyoto 6158510 Japan;

Kyoto Univ Dept Synthet Chem &

Biol Chem Kyoto 6158510 Japan;

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原文格式 PDF
正文语种 eng
中图分类应用化学;
关键词
allylation; allylic compounds; boron; ruthenium; stereoselective synthesis;

机译：allylation;烯丙基化合物;硼;钌;立体选择合成;

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专利

1. Synthesis of gamma-Boryl-Substituted Homoallylic Alcohols with anti Stereochemistry Based on a Double-Bond Transposition [J] . Miura Tomoya, Nakahashi Junki, Sasatsu Takanori, Angewandte Chemie . 2019,第4期

机译：基于双键输液的抗立体化学合成γ-硼酸γ取代的主体醇
2. Enantioselective Synthesis of Anti Homoallylic Alcohols from Terminal Alkynes and Aldehydes Based on Concomitant Use of a Cationic Iridium Complex and a Chiral Phosphoric Acid [J] . Tomoya Miura, Yui Nishida, Masao Morimoto, Journal of the American Chemical Society . 2013,第31期

机译：基于同时使用阳离子铱络合物和手性磷酸的末端炔烃和醛对映体合成对氨基醇
3. Facile synthesis of (Z)-anti-homoallylic alcohols from 3-(pinacolatoboryl)allyl alcohols, aldehydes, and triorganoboranes via a palladium-catalyzed three-component reaction [J] . Horino Yoshikazu, Aimono Ataru, Minoshima Naoki, Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2016,第31期

机译：通过钯催化的三组分反应，由3-（频哪醇硼硼基）烯丙基醇，醛和三有机硼烷轻松合成（Z）-反均丙醇
4. Stereoselective Synthesis of δ-Silyl-Substituted anti-Homoallylic Alcohols Using Palladium-Catalyzed Three-Component Reaction [C] . MURAKAMI Miki, HORINO Yoshikazu, ABE Hitoshi 日本化学会春季年会講演予稿集 . 2018

机译：使用钯催化的三组分反应的δ-甲硅烷基取代的抗官能醇的立体选择性合成
5. Part I. One-pot synthesis of secondary alcohols and one-pot asymmetric synthesis of secondary propargylic alcohols. Part II. Redox isomerization of secondary propargylic alcohols to enones. Part III. Synthesis study towards C9-C14 fragment of (+)-discodermolide. Part IV. Asymmetric synthesis of anti, anti-stereotriad building blocks for polypropionate natural products [D] . Xie, Qiuzhe 2007

机译：第一部分：仲醇的一锅法合成和仲炔丙醇的一锅法不对称合成。第二部分仲炔丙醇的氧化还原异构化为烯酮。第三部分（+）-discodermolide C9-C14片段的合成研究。第四部分聚丙烯酸酯天然产物的抗，抗立体三环构建基的不对称合成
6. Barbier-type anti-Diastereo- and Enantioselective Synthesis of β-Trimethylsilyl Fluorinated Methyl Phenylthio Homoallylic Alcohols [O] . Rui Guo, Qin Yang, Qinshan Tian, -1

机译：Barbier型抗-非对映体和对映体选择性合成β-三甲基甲硅烷基氟化甲基苯硫基均烯丙基醇
7. Synthesis of γ‐Boryl‐Substituted Homoallylic Alcohols with anti Stereochemistry Based on a Double‐Bond Transposition [O] . Tomoya Miura, Junki Nakahashi, Takanori Sasatsu, 2018

机译：基于双键输液的抗立体化学合成γ-硼酸γ取代的主体醇
8. Enolboration 7. Dicyclohexyliodoborane, a Highly Stereoselective Reagent For theEnolboration Of Tertiary Amides. Effects of Solvent And Aldolization Temperature on Stereochemistry Achieving the Stereoselective Synthesis of Either Syn or Anti Aldols [R] . Ganesan, K., Brown, H. C. 1994

机译：配合7.二环己基碘硼烷，一种高立体选择性试剂，用于叔酰胺的合成。溶剂和醛醇化温度对立体化学实现syn或anti aldols立体选择性合成的影响

Synthesis of gamma-Boryl-Substituted Homoallylic Alcohols with anti Stereochemistry Based on a Double-Bond Transposition

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