Abstract
New chroman-4-ones with gem-difluoroalkyl side chains in position 2 are easily accessible in five steps from salicylaldehyde-type derivatives. The crucial intermediates are propargylic alcohols bearing a CF2R substituent on the triple bond and the key step is their based-mediated isomerization into the corresponding enones. After MOM deprotection, an intramolecular oxa-Michael addition affords the target molecules in good overall yields. Such chromanones appear as useful intermediates for the preparation of bioactive oxygen-containing heterocycles with gem-difluoroalkyl side chains.
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