Asymmetric Michael addition of α-fluoro-α-phenylsulfonyl ketones to nitroolefins catalyzed by phenylalanine-based bifunctional thioureas

Phenylalanine-based bifunctional thiourea derivatives promoted the asymmetric Michael addition of α-fluoro-α-phenylsulfonyl ketones to nitroolefins, affording enantiomerically enriched fluorine-containing multifunctional molecules containing adjoining chiral fluorine-substituted quaternary and tertiary centers in good yields and enantioselectivities.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Phenylalanine-based bifunctional thiourea derivatives promoted the asymmetric Michael addition of α-fluoro-α-phenylsulfonyl ketones to nitroolefins with good to excellent yield and stereoselectivity. ► A possible transition state model was proposed to explain the stereochemical results of the Michael addition. ► The bifunctional chiral thiourea catalyst activated the nitroolefin through H-bonding.