Herein, we present
the first example of synthesis of 3,4-dihydropyran-2-ones
from cinnamic thioesters via a stereoselective phase-transfer-catalyzed
domino Michael–cyclization reaction with acetylacetone. The
reaction proceeded under the catalysis of Cinchona-derived quaternary ammonium phenoxide that, in combination with
inorganic bases, provided 3,4-dihydropyran-2-ones in yields of up
to 93% and enantioselectivities of up to 88% enantiomeric excess.
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