Pyrrolidinone-fused cyclohexenones by regioselective dearomatising anionic cyclisation of 2-, 3- or 4-methoxybenzamides

J. Clayden*, K. Tchabanenko, S. A. Yasin, M. D. Turnbull

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

35 Citations (Scopus)

Abstract

On treatment with t-BuLi in the presence of HMPA, 2-, 3- or 4-methoxybenzamides (o-, m- or p-anisamides) bearing N-benzyl substituents cyclise with dearomatisation to give methyl dienyl ethers which hydrolyse to give single stereo- and regioisomers of pyrrolidine-fused cyclohexenones. The bicyclic enones are versatile synthetic intermediates which undergo transformations such as stereoselective reduction and conjugate addition, regioselective Baeyer-Villiger oxidation, bromination and hydrogenation.

Original languageEnglish
Pages (from-to)302-304
Number of pages3
JournalSYNLETT
Issue number2
DOIs
Publication statusPublished - 2001

Keywords

  • Amide
  • Cyclisation
  • Enone
  • Lithiation
  • Regioselectivity

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