ol8b03881_si_001.pdf (11.24 MB)
Tandem Transformations via Friedel–Crafts Acylation Followed by a Ring-Expansion, Ring-Opening, and Cycloisomerization Sequence
journal contribution
posted on 2019-01-23, 21:20 authored by Hun Young Kim, Kyungsoo OhA tandem synthetic
route to a diverse array of cyclic compounds
has been developed from Friedel–Crafts acylation of alkynes
followed by the microwave irradiation of β-chlorovinyl ketone
intermediates. The stereoisomeric β-chlorovinyl ketone intermediates
smoothly underwent a thermal α-vinyl enolization and ring expansion
to vinyl and carbocyclic furans as well as cyclopetene derivatives
in good to excellent yields without the need for any catalysts.
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Cycloisomerization Sequencetandem Transformationscyclic compoundsarrayα- vinyl enolizationstereoisomeric β- chlorovinyl ketone intermediatescyclopetene derivativesacylationβ- chlorovinyl ketone intermediatesyieldFriedelring expansionmicrowave irradiationRing-OpeningFollowedalkynecarbocyclic furansAcylationRing-Expansioncatalyst
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