Synlett 2003(2): 0179-0182
DOI: 10.1055/s-2003-36800
LETTER
© Georg Thieme Verlag Stuttgart · New York

Electron Deficient Dienes 3: [1] Rapid Access to 2-Hydroxybenzophenones
via Inverse Electron Demand Diels-Alder-Driven Domino Reactions of a
Chromone-Fused Electron Deficient Diene with Enamines

Graham J. Bodwell*, Krista M. Hawco, Robin P. da Silva
Chemistry Department, Memorial University of Newfoundland, St. John’s, NL, A1B 3X7, Canada
Fax: +1(709)7373702; e-Mail: gbodwell@mun.ca;
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Publication History

Received 9 August 2002
Publication Date:
22 January 2003 (online)

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Abstract

Horner-Wadsworth-Emmons reaction of 3-formylchromone affords an electron deficient 1,3-diene that undergoes domino inverse electron demand Diels-Alder/elimination/intramolecular elimination reactions with enamines to afford functionalized 2-hydroxybenzophenones.