EFFICIENT SYNTHESIS OF 3-SUBSTITUTED LACTAMS USING MEERWEIN ESCHENMOSER CLAISEN [3,3] SIGMATROPIC REARRANGEMENTS

B COATES, D MONTGOMERY, PJ STEVENSON, Paul Stevenson

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13 Citations (Scopus)

Abstract

3-Allyl substituted five, six, and seven membered ring lactams are readily available in good yields and reasonable selectivity by a formal Meerwein Eschenmoser Claisen [3,3] rearrangement, using the readily available N,N-dialkylalkoxymethylene iminium salts and lithium alkoxides derived from allyl alcohols.

Original languageEnglish
Pages (from-to)4199-4202
Number of pages4
JournalTetrahedron Letters
Volume32
Issue number33
Publication statusPublished - 12 Aug 1991

Keywords

  • [3,3] SIGMATROPIC REARRANGEMENT
  • 3-SUBSTITUTED LACTAMS
  • QUARTERNARY CHIRAL CENTERS
  • STEREOCHEMICAL CONTROL

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