Gold-Catalyzed Reaction of ortho-Alkynylarylaldehydes with Conjugated Dienes: An Efficient Access to Highly Strained Tetracyclic Bridgehead Olefins

Cao Ziping; Zhu Hongbo; Meng Xin; Tian Laijin; Sun Xuejun; Chen Guang; You Jinmao

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Gold-Catalyzed Reaction of ortho-Alkynylarylaldehydes with Conjugated Dienes: An Efficient Access to Highly Strained Tetracyclic Bridgehead Olefins

机译：金催化的邻炔烷基芳醛与共轭二烯的反应：高应变四环桥头烯烃的有效途径。

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An unprecedented access to strained tetracyclic bridgehead alkenes by reaction of easily accessible ortho-alkynylarylaldehydes with conjugated dienes is described. The process involves a chemo-and stereo-selective, gold-catalyzed, tandem intermolecular [3+2] cycloaddition/Prins-type ring-closing reaction that allows generating structural complexity in a straightforward manner. This approach for the preparation of anti-Bredt compounds is synthetically superior to those previously reported: the procedure is easy to implement, operates under mild experimental conditions, is efficient, and exhibits a good substrate scope.

机译：通过容易获得的邻炔基芳基醛与共轭二烯的反应，前所未有地获得了应变四环桥头烯烃。该过程涉及化学和立体选择性，金催化的串联分子间[3 + 2]环加成/ Prins型闭环反应，该反应可直接产生结构复杂性。这种制备抗Bredt化合物的方法在合成上优于先前报道的方法：该方法易于实施，在温和的实验条件下操作，有效且具有良好的底物范围。

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《Chemistry: A European journal》 |2016年第27期|共5页
作者
Cao Ziping; Zhu Hongbo; Meng Xin; Tian Laijin; Sun Xuejun; Chen Guang; You Jinmao;
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正文语种 eng
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关键词
alkynylbenzylaldehyde; bridgehead; diene; gold; polycycles;

机译：炔基苄醛;桥头;二烯;金;多环;

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1. Gold-Catalyzed Reaction of ortho-Alkynylarylaldehydes with Conjugated Dienes: An Efficient Access to Highly Strained Tetracyclic Bridgehead Olefins [J] . Cao Ziping, Zhu Hongbo, Meng Xin, Chemistry: A European journal . 2016,第27期

机译：金催化的邻炔烷基芳醛与共轭二烯的反应：高应变四环桥头烯烃的有效途径。
2. Access to tetracyclic aromatics with bridgehead metals via metalla-click reactions [J] . Zhengyu Lu, Qin Zhu, Yuanting Cai, Science Advances . 2020,第3期

机译：通过Metalla键反应访问桥头金属的四环芳烃
3. Highly Efficient Access to Bi- and Tricyclic Ketals through Gold-Catalyzed Tandem Reactions of 4-Acyl-1,6-diynes [J] . Meng J, Zhao YL, Ren CQ, Chemistry: A European journal . 2009,第8期

机译：通过金催化的4-Acyl-1,6-diynes串联反应高效获得双环和三环缩酮
4. Advances and Limits in Copolymerization of Olefins with Conjugated Dienes [C] . Christophe Boisson, Vincent Monteil, Julien Thuilliez, World Polymer Congress . 2005

机译：缀合二烯的烯烃共聚的进展和限制
5. Efforts towards the total synthesis of natural product alkaloids (+/-) lycorine and gracilamine, gold-catalyzed diene formation, and oxy-Ccope/ene/Claisen/Diels-Alder reactions to form the homo-steroid skeleton. [D] . Chartrand, Anik Michelle. 2010

机译：努力全天然合成天然生物碱（+/-）lycorine和gracilamine，金催化的二烯形成以及oxy-Ccope / ene / Claisen / Diels-Alder反应以形成类固醇骨架。
6. Access to tetracyclic aromatics with bridgehead metals via metalla-click reactions [O] . Zhengyu Lu, Qin Zhu, Yuanting Cai, 2020

机译：通过金属点击反应获得桥头金属与四环芳烃的关系
7. Highly Efficient Access to Strained Bicyclic Ketals via Gold-Catalyzed Cycloisomerization of Bis-homopropargylic Diols [O] . -1

机译：通过黄金催化的双相丙基二醇的金催化环机化高效地获得紧张双环酮
8. Hexamethylsilirane. 5. Conversion to Five-Membered Ring Silicon Compounds by 'Two-Atom' Insertion Reactions of Aryl Olefins, 1,3-Dienes, and Conjugated Acetylenes [R] . Seyferth, D., Duncan, D. P., Shannon, M. L., 1984

机译：Hexamethylsilirane。 5.通过芳烃烯烃，1,3-二烯和共轭炔烃的“双原子”插入反应转化为五元环硅化合物

Gold-Catalyzed Reaction of ortho-Alkynylarylaldehydes with Conjugated Dienes: An Efficient Access to Highly Strained Tetracyclic Bridgehead Olefins

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