Enantioselective alpha-fluorination of aldehydes using chiral organic catalysts
AssigneeCalifornia Institute of Technology
InventorsDavid MacMillan, Teresa Beeson
Life of this patent
Estimating the term…
Abstract
Nonmetallic, chiral organic catalysts are used to catalyze enantioselective fluorination of enolizable aldehydes. Reaction systems composed of an enolizable aldehyde, an electrophilic fluorination reagent, and a nonmetallic chiral catalyst in the form of an imidazolidinone salt are also provided.
Claims20
A method for the enantioselective fluorination of an aldehyde, comprising contacting an enolizable aldehyde with a fluorination reagent in the presence of a catalytically effective amount of a nonmetallic chiral catalyst containing a Group 15 or Group 16 heteroatom.
The method of claim 2, wherein the enolizable aldehyde has the structure of formula (I)
- in which R1 and R2 are independently selected from hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, and functional groups.
A reaction system comprising an enolizable aldehyde, an electrophilic fluorination reagent, and a nonmetallic chiral catalyst comprising an imidazolidinone salt having the structure of formula (III) or (IV)
- wherein:
- R5 is selected from hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, and substituted heteroatom-containing hydrocarbyl;
- R6 and R7 are independently selected from hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, and functional groups;
- R8 is selected from hydrogen, halo, hydroxyl, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl;
- R9 is selected from hydrogen, halo, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl;
- R10 is a cyclic group, either unsubstituted or substituted with 1 to 4 non-hydrogen substituents and containing zero to 3 heteroatoms;
- HX is a Brönsted acid;
- and
- n is zero or 1.
Dependencies are inferred from the claim text.