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US 8,912,341 B2Granted
Enantioselective N-heterocyclic carbene-catalyzed annulation reactions with imidazolidinones
AssigneeNorthwestern University
InventorsKarl A. Scheidt, Elizabeth O. McCusker
Life of this patent
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Abstract
Enantiomeric bicyclic lactone compounds as can be prepared via an N-heterocyclic carbene-catalyzed annulation reaction.
Claims20
A method of preparing a bicyclic lactone compound, said method
- comprising:
- providing a mixture of a heterocyclic alkylidene imidazolidinone, a triazolium N-heterocyclic carbene catalyst precursor compound and a base component, said alkylidene imidazolidinone of a formula
- wherein Ar is selected from aryl and substituted aryl moieties, said Ar substituents selected from alkyl, alkoxy, halo and haloalkyl substituents and combinations thereof, and R1 is selected from aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkyl and cycloalkyl moieties, said R1 substituents selected from alkyl, alkoxy, halo and haloalkyl substituents and combinations thereof;
- and
- introducing to said mixture an α,β-unsaturated aldehyde in the presence of an acid component, said aldehyde of a formula
- wherein R2 is selected from H, alkyl, cycloalkyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl moieties, said R2 substituents selected from alkyl, alkoxy and halo substituents and combinations thereof, to provide a bicyclic lactone compound of a formula or a salt thereof
3 more elements
A method of using a heterocyclic conjugate acceptor component to prepare a bicyclic lactone compound of a formula
- said method comprising:
- providing a mixture of a heterocyclic alkylidene imidazolidinone, a triazolium N-heterocyclic carbene catalyst precursor compound and a base component, said alkylidene imidazolidinone of a formula
- wherein Ar is selected from aryl and substituted aryl moieties, said Ar substituents selected from alkyl, alkoxy, halo and haloalkyl substituents and combinations thereof, and R1 is selected from aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkyl and cycloalkyl moieties, said R1 substituents selected from alkyl, alkoxy, halo and haloalkyl substituents and combinations thereof;
- introducing to said mixture an α,β-unsaturated aldehyde in the presence of an acid component, said aldehyde of a formula
- wherein R2 is selected from H, alkyl, cycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl moieties, said R2 substituents selected from alkyl, alkoxy and halo substituents and combinations thereof, to couple said components;
- and
- intramolecular O-acylation of said imidazolidinone to provide said bicyclic lactone compound or a salt thereof.
4 more elements
A compound selected from compounds of a formula
- wherein Ar is selected from aryl and substituted aryl moieties, said Ar substituents selected from alkyl, alkoxy, halo and haloalkyl substituents and combinations thereof;
- R1 is selected from aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkyl and cycloalkyl moieties, said R1 substituents selected from alkyl, alkoxy, halo and haloalkyl substituents and combinations thereof;
- and R2 is selected from H, alkyl, cycloalkyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl moieties, said R2 substituents selected from alkyl, alkoxy and halo substituents and combinations thereof, and salts thereof.
A compound selected from compounds of a formula
- wherein Ar is selected from aryl and substituted aryl moieties, said Ar substituents selected from alkyl, alkoxy, halo and haloalkyl substituents and combinations thereof;
- R1 is selected from aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkyl and cycloalkyl moieties, said R1 substituents selected from alkyl, alkoxy, halo and haloalkyl substituents and combinations thereof;
- and R2 is selected from H, alkyl, cycloalkyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl moieties, said R2 substituents selected from alkyl, alkoxy and halo substituents and combinations thereof, and salts thereof.
Dependencies are inferred from the claim text.