Enantioselective chlorination and fluorination of beta-keto phosphonates catalyzed by chiral Lewis acids.
The direct chiral Lewis acidic enantioselective chlorination and fluorination of beta-keto phosphonates is presented; the chlorination proceeds in high yields and with up to 94% ee using NCS as the chloro source, while the fluorination with (PhSO2)2NF (NFSI) gives the optically active alpha-fluoro-beta-keto phosphonates in moderate to good yields and with up to 91% ee.
Bernardi
Luca
L
Danish National Research Foundations: Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000, Aarhus C, Denmark.
Jørgensen
Karl Anker
KA
D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D008024:Ligands; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry; D012538:Scandium / Q000737:chemistry*; D013237:Stereoisomerism; D013388:Succinimides / Q000737:chemistry*; D013449:Sulfonamides / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry*
D007659:Ketones; D008024:Ligands; D009942:Organometallic Compounds; D063065:Organophosphonates; D013388:Succinimides; D013449:Sulfonamides; C517788:fluorodi(phenylsulfonyl)amine; C015752:N-chlorosuccinimide; D003300:Copper; D015032:Zinc; D012538:Scandium