Synthesis of donor-acceptor alkynylcyclopropanes by diastereoselective cyclopropanation of electron-deficient alkenes with alkoxyalkynyl Fischer carbene complexes

Barluenga J; Fernandez-Rodriguez MA; Garcia-Garcia P; Aguilar E; Merino I

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Synthesis of donor-acceptor alkynylcyclopropanes by diastereoselective cyclopropanation of electron-deficient alkenes with alkoxyalkynyl Fischer carbene complexes

机译：电子不足的烯烃与烷氧基炔基菲舍尔卡宾配合物的非对映选择性环丙烷化反应，合成供体-受体炔基环丙烷

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The reaction of electron-deficient alkenes with alkoxyalkynyl Fischer carbene complexes (FCCs) represents a straightforward route to a new type of captodative (donor-acceptor) alkynylcyclopropanes, which have been prepared in moderate to high yields and in a diastereoselective manner. Some studies regarding the employment of additives to facilitate the recovery of the metal moiety after the reaction are also described. Finally, the first example of a cyclopropanation reaction through employing Fischer carbene complexes under microwave irradiation is presented; this method proved to be an advantageous alternative to the thermal reaction.

机译：电子不足的烯烃与烷氧基炔基菲舍尔卡宾配合物（FCC）的反应代表了一种新型的俘获性（供体-受体）炔基环丙烷的直接路线，该方法以中等至高收率和非对映选择性的方式制备。还描述了一些有关使用添加剂以促进反应后金属部分回收的研究。最后，给出了在微波辐射下通过使用费歇尔卡宾配合物进行环丙烷化反应的第一个实例。该方法被证明是热反应的有利替代方案。

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《Chemistry: A European journal》 |2005年第1期|共11页
作者
Barluenga J; Fernandez-Rodriguez MA; Garcia-Garcia P; Aguilar E; Merino I;
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正文语种 eng
中图分类化学;
关键词
carbene ligands; carbenes; cyclopropanation; diastereoselectivity; microwave-accelerated reactions; TRANSITION-METAL-COMPLEXES; ORGANIC-SYNTHESIS; SUBSTITUTED CYCLOPROPANES; MICROWAVE IRRADIATION; ENOL ETHERS; VINYLCYCLOPROPANE DERIVATIVES; STEREOSELECTIVE-SYNTHESIS; CYCLOADDITION REACTIONS; CYCLIZATION REACTIONS; ASYMMETRIC-SYNTHESIS;

机译：卡宾配体;卡宾;环丙烷化;非对映选择性;微波加速反应;过渡金属-络合物;有机合成;取代环丙烷;微波辐照;烯醇;环丙烷基;环合反应;立体选择性;固相反应;

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1. Synthesis of Donor-Acceptor Alkynylcyclopropanes by Diastereoselective Cyclopropanation of Electron-Deficient Alkenes with Alkoxyalkynyl Fischer Carbene Complexes [J] . Jose Barluenga, Manuel A.Fernandez-Rodriguez, Patricia Garcia-Garcia, Chemistry: A European journal . 2006,第1期

机译：电子不足的烯烃与烷氧基炔基菲歇尔配合物的非对映选择性环丙烷化合成给体-受体炔基环丙烷
2. Synthesis of Donor-Acceptor Alkynylcyclopropanes by Diastereoselective Cyclopropanation of Electron-Deficient Alkenes with Alkoxyalkynyl Fischer Carbene Complexes [J] . Jose Barluenga, Manuel A.Fernandez-Rodriguez, Patricia Garcia-Garcia, Chemistry: A European journal . 2006,第1期

机译：电子不足的烯烃与烷氧基炔基菲歇尔配合物的非对映选择性环丙烷化合成给体-受体炔基环丙烷
3. Synthesis of donor-acceptor alkynylcyclopropanes by diastereoselective cyclopropanation of electron-deficient alkenes with alkoxyalkynyl Fischer carbene complexes [J] . Barluenga J, Fernandez-Rodriguez MA, Garcia-Garcia P, Chemistry: A European journal . 2005,第1期

机译：电子不足的烯烃与烷氧基炔基菲舍尔卡宾配合物的非对映选择性环丙烷化反应，合成供体-受体炔基环丙烷
4. Cyclopropanation Reaction by Addition of Diiodomethyl p-Tolyl Sulfone (DMTS) or Iodoform to Electron-deficient Alkenes [C] . Kahori Tamura, Minori Takino, Shoji Matsumoto 日本化学会春季年会講演予稿集 . 2018

机译：通过加入二碘甲基对甲砜（DMT）或碘化物的环丙烷反应至电子缺乏烯烃
5. Fischer chromium carbenes in organic synthesis: Metathesis reactions of Fischer carbene complexes with isonitriles. [D] . Burns, Ellen Elizabeth. 1995

机译：有机合成中的Fischer铬碳酸酯：Fischer卡宾配合物与异腈的复分解反应。
6. Synthesis of highly substituted benzene ring systems through three-component coupling of enyne imines Fischer carbene complexes and electron-deficient alkynes [O] . Bishnu Dhakal, Lalith S. R. Gamage, Yanshi Zhang, -1

机译：通过烯炔亚胺菲舍尔卡宾配合物和缺电子炔烃的三组分偶联合成高度取代的苯环系统
7. Diastereoselective Cyclopropanation of Ketone Enols with Fischer Carbene Complexes [O] . -1

机译：酮烯醇与费 - 卡宾复合物的ketone enols的反映选择环丙酮
8. Ylide-Carbene Chemistry. Synthesis of 1,1-Difluoro-1-alkenes [R] . Wheaton, G. A., Burton, D. J. 1983

机译：Ylide-Carbene化学。 1,1-二氟-1-烯烃的合成

Synthesis of donor-acceptor alkynylcyclopropanes by diastereoselective cyclopropanation of electron-deficient alkenes with alkoxyalkynyl Fischer carbene complexes

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