摘要
The gold(I)-catalyzed cyclization of the cyclohexa-1,3-diene bearing a terminal alkyne and a gemdiester in the tether proceeds via a cationic gold intermediate to give a tetrahydromethyleneindene derivative. Changing the gem-diester to a gem-diketone in the tether, the transient gold-stabilized carbocation is trapped intramolecularly by a methyl ketone to afford a tricyclo[5.4.04,8]undecane ring skeleton. Under the same reaction conditions, aryl-substituted cyclohexadienynes afford hexahydroacephenanthrylene rings in a diastereoselective fashion and in good yields. The reaction proceeded via attack of the aryl group onto the gold-stabilized carbocations followed by aromatization and protodemetalation to generate the tetracarbocycles. This cycloaddition can be applied to the synthesis of pentahydronapthoazulenes from aryl-substituted cycloheptadienynes and the gold(I) catalyst.
原文 | 英語 |
---|---|
頁(從 - 到) | 5326-5332 |
頁數 | 7 |
期刊 | Organometallics |
卷 | 27 |
發行號 | 20 |
DOIs | |
出版狀態 | 已發佈 - 2008 10月 27 |
對外發佈 | 是 |
ASJC Scopus subject areas
- 物理與理論化學
- 有機化學
- 無機化學
指紋
深入研究「Facile synthesis of carbotetracycles via gold(i)-catalyzed cyclization of unactivated cyclic 1-aryl-6,8-dien-1-ynes」主題。共同形成了獨特的指紋。資料集
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CCDC 709821: Experimental Crystal Structure Determination
Yeh, M. P. (Creator), Tsao, W. (Creator) & Lee, B. (Creator), Unknown Publisher, 2009
DOI: 10.5517/ccrtmgm, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccrtmgm&sid=DataCite
資料集: Dataset
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CCDC 709824: Experimental Crystal Structure Determination
Yeh, M. P. (Creator), Tsao, W. (Creator) & Lee, B. (Creator), Unknown Publisher, 2009
DOI: 10.5517/ccrtmkq, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccrtmkq&sid=DataCite
資料集: Dataset
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CCDC 709822: Experimental Crystal Structure Determination
Yeh, M. P. (Creator), Tsao, W. (Creator) & Lee, B. (Creator), Unknown Publisher, 2009
DOI: 10.5517/ccrtmhn, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccrtmhn&sid=DataCite
資料集: Dataset