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US 2003/0120075 A1Published application
Stereospecific enrichment of heterocyclic enantiomers
AssigneeR.T. Alamo Adventures I, LLC
InventorsStefan Kwiatkowski, Miroslaw Golinski, Joseph Kupper
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Abstract
The present invention describes methods for the stereoselective synthesis of heterocyclic enantiomers. The methods of the present invention incorporate the stereo-preferred oxidation of quinolone thiomethyl intermediates by optically active camphor based oxaziridines to provide R(+) or S(−) quinolone methylsulfinyl derivatives.
Claims4
A method, comprising:
- a) providing:
- i) a flosequinan racemate;
- ii) triphenylphosphine;
- and
- b) reacting, in a solvent, said flosequinan racemate with said triphenylphosphine under conditions such that a racemic mixture of 7-fluoro-1-methyl-3-methylthio-4-quinolone is produced.
2 more elements
A method, comprising:
- a) providing:
- i) a flosequinan racemate;
- ii) triphenylphosphine;
- and
- b) reacting, in a solvent, said flosequinan racemate with said triphenylphosphine under conditions such that a racemic mixture of 7-fluoro-1-methyl-3-methylthio-4-quinolone is produced.
- c) treating said racemic mixture of 7-fluoro-1-methyl-3-methylthio-4-quinolone with (1S)-(+)-(10-camphorsulfonyl)oxaziridine under conditions such that S-(−)-flosequinan is produced in enantiomeric excess.
3 more elements
Dependencies are inferred from the claim text.