Synthesis of 2-azaspiro[4.6]undec-7-enes from N -tosyl- N -(3-arylpropargyl)-tethered 3-methylcyclohex-2-en-1-ols

Ming-Chang P. Yeh, Chia Jung Liang, Chern Wei Fan, Wei Hang Chiu, Jun Yuan Lo

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The FeCl3-promoted synthesis of 2-azaspiro[4.6]undec-7-ene rings proceeds via ring expansion/cyclization/chlorination of N-tosyl-N-(3- arylpropargyl)-tethered 6-methylbicyclo[4.1.0]heptan-2-ols. This azaspirocyclic ring skeleton can also be obtained in one pot from the tert-butyldimethylsilyl- protected N-tosyl-N-(3-arylpropargyl)-tethered 3-methylcyclohex-2-en-1-ols and diethylzinc/diiodomethane.

Original languageEnglish
Pages (from-to)9707-9717
Number of pages11
JournalJournal of Organic Chemistry
Volume77
Issue number21
DOIs
Publication statusPublished - 2012 Nov 2

ASJC Scopus subject areas

  • Organic Chemistry

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