Synthesis of Spirolactams and Fused Bicyclic Lactams via Acid-Promoted Cyclolactamization of (Ethynyl(tosyl)amino)methyl-Tethered Cyclohex-2-enols

Po Ting Tung, Chang Zhi Zhong, Tzu Chiang Chien, Ming Chang P. Yeh

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2 引文 斯高帕斯(Scopus)

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
頁(從 - 到)11543-11557
頁數15
期刊Journal of Organic Chemistry
82
發行號21
DOIs
出版狀態已發佈 - 2017 十一月 3

ASJC Scopus subject areas

  • Organic Chemistry

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