Acid addition salts of imidazolidinones as reaction catalysts
AssigneeThe Regents of the University of California
InventorsDavid W. C. MacMillan, Kateri A. Ahrendt
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Abstract
Acid addition salts of imidazolidinones are provided as catalysts for transforming a functional group within a first reactant by reaction with a second reactant. Exemplary first reactants are α,β-unsaturated carbonyl compounds such as α,β-unsaturated ketones and α,β-unsaturated aldehydes. Chiral imidazolidinone salts can be used to catalyze enantioselective reactions, such that a chiral product is obtained from a chiral or achiral starting material in enantiomerically pure form.
Claims17
An imidazolidinone salt having the structure of formula (IV) or (IV-A)
- wherein:
- R5, R6 and R7 are independently selected from the group consisting of hydroxyl, hydrocarbyl, and substituted hydrocarbyl;
- R8 and R9 are independently selected from the group consisting of hydrido, halo, hydroxyl, hydrocarbyl, and substituted hydrocarbyl, or wherein any two or more of R5, R6, R7, R8 and R9 may be linked together to form a hydrocarbylene or a substituted hydrocarbylene bridge;
- n is 1;
- R10 is a cyclic group, either unsubstituted or substituted with substituents that may be the same or different and are selected from the group consisting of halo, hydroxyl, hydrocarbyl, and substituted hydrocarbyl;
- and
- HX is a Bronsted acid,
- wherein the imidazolidinone salt is optionally covalently bound, directly or indirectly, to a solid support.
(5S)-5-Benzyl-2,2,3-trimethylimidazolidin-4-one hydrochloride.
Dependencies are inferred from the claim text.