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

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

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
Volume82
Issue number21
DOIs
Publication statusPublished - 2017 Nov 3

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Bearings (structural)
Lactams
Skeleton
Hydration
Ions
Acids

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of Spirolactams and Fused Bicyclic Lactams via Acid-Promoted Cyclolactamization of (Ethynyl(tosyl)amino)methyl-Tethered Cyclohex-2-enols. / Tung, Po Ting; Zhong, Chang Zhi; Chien, Tzu Chiang; Yeh, Ming-Chang P.

In: Journal of Organic Chemistry, Vol. 82, No. 21, 03.11.2017, p. 11543-11557.

Research output: Contribution to journalArticle

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