Enantioselective synthesis of 3,4-dihydropyran-2-ones via PTC addition-cyclisation of acetylacetone to cinnamic thioesters.

07:00 EST 13th February 2020 | BioPortfolio

Summary of "Enantioselective synthesis of 3,4-dihydropyran-2-ones via PTC addition-cyclisation of acetylacetone to cinnamic thioesters."

Herein we present the first example of synthesis of 3,4-dihydropyran-2-ones from cinnamic thioesters via a stereoselective phase-transfer catalysed domino Michael-cyclisation 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% ee.


Journal Details

This article was published in the following journal.

Name: The Journal of organic chemistry
ISSN: 1520-6904


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