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Synlett 1999; 1999(4): 477-479
DOI: 10.1055/s-1999-2645
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Electron Deficient Dienes. 2. One Step Synthesis of a Coumarin-Fused Electron Deficient Diene and its Inverse Electron Demand Diels-Alder Reactions with Enamines

Graham J. Bodwell* , Zulan Pi, Ian R. Pottie
  • *Chemistry Department, Memorial University of Newfoundland, St. John's, Newfoundland, Canada, AlB 3X7; Fax +1(7 09)-7 37-37 02; E-mail: gbodwell@morgan.ucs.mun.ca
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Publication Date:
31 December 1999 (online)

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A coumarin-fused electron deficient diene was prepared by the base-induced reaction of dimethyl glutaconate and salicaldehyde. Its inverse electron demand Diels-Alder reactions with enamines give, after in situ elimination and dehydrogenation, benzocoumarins.

Diels-Alder - inverse electron demand - coumarins - enamines

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