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Synlett 2000; 2000(3): 415-417
DOI: 10.1055/s-2000-6531
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The Sequential Ester Dienolate [2,3]-Wittig/3-oxy-Cope Rearrangement. New Access to Substituted α-Keto Esters

Martin Hiersemann*
  • *Institut für Organische Chemie der Technischen Universität Dresden, D-01062, Germany; Fax +49 3 51 4 63 70 30; E-mail: martin.hiersemann@chemie.tu-dresden.de
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Publication History

Publication Date:
31 December 2000 (online)

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The dienolate [2,3]-Wittig rearrangement of 2-allyloxy-substituted α,β-unsaturated esters 1a-h afforded 3-alkoxycarbonyl-3-hydroxy-substituted 1,5-hexadienes 4a-h which were transformed to α-keto esters 5a-h via a thermal or Pd(II)-catalyzed oxy-Cope rearrangement. Examples for a domino dienolate [2,3]-Wittig/3-oxy Cope rearrangement and for a domino oxy-Cope rearrangement/ene reaction are reported.

rearrangements - pericyclic reactions - α-keto esters - dienolates - domino reactions

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