Journal
TETRAHEDRON
Volume 60, Issue 5, Pages 1049-1055Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2003.11.083
Keywords
chroman-2-ones; Michael addition; Horner-Wadsworth-Emmons olefination
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3-Methylidenechroman-2-ones, or their rearrangement products 3-methylchromen-2-ones, were efficiently synthesized by Michael addition of various nucleophiles to 3-diethoxyphosphorylchromen-2-ones followed by Horner-Wadsworth-Emmons reaction of the adducts with formaldehyde. Relative configuration and conformation of the intermediate adducts were studied using NMR spectroscopy and semiempirical PM3 calculations. (C) 2003 Elsevier Ltd. All rights reserved.
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