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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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.

Original languageEnglish
Pages (from-to)11543-11557
Number of pages15
JournalJournal of Organic Chemistry
Issue number21
Publication statusPublished - 2017 Nov 3


ASJC Scopus subject areas

  • Organic Chemistry

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