Abstract
In a straightforward and fast protocol, a mixture of 1,3-dimethylimidazolium fluoride ([DMIM]F) and 1-butylimidazolium tetrafluoroborate ([Hbim]BF4) efficiently catalyzed the reaction of epoxides with ketene silyl acetals (KSA) to give various γ-lactones under metal-free conditions. Diverse kinds of the desired γ-lactones were directly prepared with high regioselectivities and yields in a simple one-pot procedure using [DMIM]F as Si–O bond activator and [Hbim]BF4 as solvent and acidic ionic liquid catalyst. The ionic liquid mixture was recovered and reused three times and no loss in its activity was observed.
Highlights
The reactions reactions of ofepoxides epoxidesand andcarboanion carboanionnucleophiles nucleophiles very important transformations in areare very important transformations in the the synthesis of biologically significant targets [1,2,3].OneOneofofthe themost mostimportant importantof ofthese thesereactions reactions is the synthesis of biologically significant targets [1,2,3].reaction enolates of ketones and esters esters with with epoxides epoxides [4,5].[4,5]
Oneofofthe themost mostimportant importantof ofthese thesereactions reactions is the synthesis of biologically significant targets reaction enolates of ketones and esters esters with with epoxides epoxides [4,5]
([Hbim]BF4 ) as solvent and acidic ionic liquid catalyst for the preparation of various γ-lactones the reaction of epoxides with KSA under metal-free conditions
Summary
The reactions reactions of ofepoxides epoxidesand andcarboanion carboanionnucleophiles nucleophiles very important transformations in areare very important transformations in the the synthesis of biologically significant targets [1,2,3].One. The use of KSA as an alternative for unreactive ester enolates affords a carboanion reactive toward epoxides to furnish γ-lactone products if an effective catalyst is used. Chemical libraries of drug-like heterocyclic compounds [21,22,23,24] In this context, we wish to report task-specific ionic liquid, 1,3-dimethylimidazolium fluoride ([Dmim]F) as a new efficient and reusable Si–O bond activator and butylimidazolium tetrafluoroborate ([Hbim]BF4) as solvent and acidic ionic liquid catalyst for the preparation of various γ-lactones from ([Hbim]BF4 ) as solvent and acidic ionic liquid catalyst for the preparation of various γ-lactones the reaction of epoxides with KSA under metal-free conditions.
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