Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1314324 | Journal of Fluorine Chemistry | 2012 | 7 Pages |
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.