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Synlett 2000; 2000(8): 1208-1209
DOI: 10.1055/s-2000-6742
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Diastereoselective Preparation of cis-2-Substituted 3-Ethenyl Prolines via [3,2]-Sigmatropic Rearrangements of Didehydropiperidinium Ylids

Jerome F. Hayes* , Ali Tavassoli, J. B. Sweeney
  • *SmithKline Beecham Pharmaceuticals, Old Powder Mills, Leigh, Tonbridge, TN11 9AN, UK; E-mail: j.b.sweeney@reading.ac.uk
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Publication Date:
31 December 2000 (online)

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The [3,2]-sigmatropic rearrangements of N-(methoxycarbonyl)methyl-N-methyl-1,2,3,6-tetrahydropyridinium bromide (1a) has been extrapolated to allow preparation of (±)-cis-2-aryl-3-ethenyl prolines, and certain spiro-prolines.

[3,2]-sigmatropic rearrangements - kainoids - NMDA

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