摘要
A simple synthetic method to construct the spirolactam framework from TfOH-catalyzed spirolactamization of cyclohex-2-enols bearing a tethered (arylethynyl(tosyl)amino)methyl moiety is described. The reaction proceeded through a keteniminium-allylic carbocation intermediate. Hydration of the keteniminium ion, followed by attack of the resulting enolate onto the tethered allylic carbocation, provided the spirolactam ring skeleton. This strategy could also be employed in the synthesis of fused bicyclic lactams from BF3·OEt2-assisted cyclolactamization of TBS-protected 2-(ethynyl(tosyl)amino)methylcyclohex-2-enols.
原文 | 英語 |
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頁(從 - 到) | 11543-11557 |
頁數 | 15 |
期刊 | Journal of Organic Chemistry |
卷 | 82 |
發行號 | 21 |
DOIs | |
出版狀態 | 已發佈 - 2017 11月 3 |
ASJC Scopus subject areas
- 有機化學
指紋
深入研究「Synthesis of Spirolactams and Fused Bicyclic Lactams via Acid-Promoted Cyclolactamization of (Ethynyl(tosyl)amino)methyl-Tethered Cyclohex-2-enols」主題。共同形成了獨特的指紋。資料集
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CCDC 1491136: Experimental Crystal Structure Determination
Tung, P. (Creator), Zhong, C. (Creator), Chien, T. (Creator) & Yeh, M. P. (Creator), Unknown Publisher, 2017
DOI: 10.5517/ccdc.csd.cc1m1n5h, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1m1n5h&sid=DataCite
資料集: Dataset
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CCDC 1553347: Experimental Crystal Structure Determination
Tung, P. (Creator), Zhong, C. (Creator), Chien, T. (Creator) & Yeh, M. P. (Creator), Unknown Publisher, 2017
DOI: 10.5517/ccdc.csd.cc1p4cz5, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1p4cz5&sid=DataCite
資料集: Dataset
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CCDC 1491138: Experimental Crystal Structure Determination
Tung, P. (Creator), Zhong, C. (Creator), Chien, T. (Creator) & Yeh, M. P. (Creator), Unknown Publisher, 2017
DOI: 10.5517/ccdc.csd.cc1m1n7k, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1m1n7k&sid=DataCite
資料集: Dataset