Ruthenium-Catalyzed One-Pot Double Allylation/Cycloisomerization of 1,3-Dicarbonyl Compounds Leading to exo-Methylenecyclopentanes

Yoshihiko Yamamoto; Yu-ichiro Nakagai; Kenji Itoh

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Ruthenium-Catalyzed One-Pot Double Allylation/Cycloisomerization of 1,3-Dicarbonyl Compounds Leading to exo-Methylenecyclopentanes

机译：钌催化的1,3-二羰基化合物的一锅双烯丙基化/环异构化，导致外亚甲基环戊烷

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The ruthenium-catalyzed one-pot double allylation/cycloisomerization of 1,3-diketones and methyl acetoacetate gave exo-methylenecyclopen tanes in moderate to good yields with high isomer selectivity.The double allylation step effectively proceeded in the presence of a Ru~(II)precatalyst,[Cp~*RuCl(cod)],in 1,2-dichloroethane at 90 deg C.Te subsequent cycloisomerization was carried out upon addition of triethylsilane as a hydride source without purification of a 1,6-diene intermediate.Detailed inspections of the reaction by ~1H NMR spectroscopy disclosed that triethylsilyl methyl ether plays an important role for the conversion of a ruthenium(IV)alyl complex formed in the double allylation step into a ruthenium(II)species required for the cycloisomerization.

机译：钌催化的1,3-二酮和乙酰乙酸甲酯的一锅双烯丙基化/环异构化反应可中等至良好的收率和高异构体选择性地制得亚甲基环戊烷单双烯丙基化反应。催化剂，[Cp〜* RuCl（cod）]，在90℃下于1,2-二氯乙烷中进行。随后，在不纯化1,6-二烯中间体的情况下，通过添加三乙基硅烷作为氢化物源，进行随后的环异构化。详细通过〜1H NMR光谱对反应的检查发现，三乙基甲硅烷基甲基醚对于将在双烯丙基化步骤中形成的钌（IV）烷基络合物转化为环异构化所需的钌（II）物种起着重要作用。

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《Chemistry: A European journal》 |2004年第1期|共6页
作者
Yoshihiko Yamamoto; Yu-ichiro Nakagai; Kenji Itoh;
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正文语种 eng
中图分类化学;
关键词
alkenes; allylation; cycloisomerization; homogeneous catalysis; ruthenium;

机译：烯烃;烯丙基化;环异构化;均相催化;钌;

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1. Ruthenium-Catalyzed One-Pot Double Allylation/Cycloisomerization of 1,3-Dicarbonyl Compounds Leading to exo-Methylenecyclopentanes [J] . Yoshihiko Yamamoto, Yu-ichiro Nakagai, Kenji Itoh Chemistry: A European journal . 2004,第1期

机译：钌催化的1,3-二羰基化合物的一锅双烯丙基化/环异构化，导致外亚甲基环戊烷
2. A novel propargylation/cycloisomerization tandem process catalyzed by a ruthenium(II)/trifluoroacetic acid system: One-pot entry to fully substituted furans from readily available secondary propargylic alcohols and 1,3-dicarbonyl compounds [J] . Cadierno V, Gimeno J, Nebra N Advanced synthesis & catalysis . 2007,第3期

机译：钌（II）/三氟乙酸系统催化的新型丙基丙烯酸/环旋异构化串联方法：单罐进入从易于可获得的二次丙醇醇和1,3-二羰基化合物的完全取代呋喃
3. Bronsted acid ionic liquid-catalyzed direct benzylation, allylation and propargylation of 1,3-dicarbonyl compounds with alcohols as well as one-pot synthesis of 4H-chromenes [J] . Funabiki K, Komeda T, Kubota Y, Tetrahedron . 2009,第36期

机译：布朗斯台德酸离子液体催化1,3-二羰基化合物与醇的直接苄基化，烯丙基化和炔丙基化以及一锅合成4H-色烯
4. A one-pot synthesis of functionalized 1,3-thiazoles from thioamides and 2-chloro-1,3-dicarbonyl compounds in an ionic liquid [C] . Issa Yavari, S. Zahra Sayyed-Alangi, Rahimeh Hajinasiri European Symposium on Organic Chemistry . 2009

机译：离子液体中硫胺和2-氯-1,3-二羰基化合物的官能化1,3-噻唑的单罐合成
5. Oxidative Transformations of 1,3-Dicarbonyl Compounds by IBX in Various Solvent Systems [D] . Poreddy, Shashidhar. 2016

机译：IBX在各种溶剂系统中的1,3-二羰基化合物的氧化转化
6. Et3B-mediated and palladium-catalyzed direct allylation of β-dicarbonyl compounds with Morita–Baylis–Hillman alcohols [O] . Ahlem Abidi, Yosra Oueslati, Farhat Rezgui 2016

机译：Et3B介导和钯催化的β-二羰基化合物与Morita–Baylis–Hillman醇的直接烯丙基化
7. Metal Triflate-Catalyzed Cationic Benzylation and Allylation of 1,3-Dicarbonyl Compounds [O] . -1

机译：金属三氟乙酯催化阳离子苄基化和1,3-二羰基化合物的烯丙基化合物

Ruthenium-Catalyzed One-Pot Double Allylation/Cycloisomerization of 1,3-Dicarbonyl Compounds Leading to exo-Methylenecyclopentanes

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