title: Assembly of Fluorinated Quaternary Stereogenic Centers through Catalytic Enantioselective Detrifluoroacetylative Aldol Reactions.
abstract: A Cu-catalyzed asymmetric detrifluoroacetylative aldol addition reaction of 2-fluoro-1,3-diketones/hydrates to aldehydes in the presence of base and chiral bidentate ligand was developed. The reaction was carried out under convenient conditions and tolerated a wide range of substrates, resulting in fluorinated quaternary stereogenic α-fluoro-β-hydroxy ketone products with good chemical yields, diastereo- and enantioselectivities. This catalytic asymmetric detrifluoroacetylative aldol addition reaction provides a new approach for the preparation of biologically relevant products containing C-F quaternary stereogenic centers.
authors: School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, 22 Hankou Road, Nanjing, 210093 (China).
authors: Chen
authors: C
authors: Xie
authors: Lingmin
authors: L
authors: Wu
authors: Jianlin
authors: J
authors: Han
authors: Vadim A
authors: VA
authors: Soloshonok
authors: Yi
authors: Y
authors: Pan
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D054879:Halogenation; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D006845:Hydrocarbons, Fluorinated; D007659:Ketones; D009942:Organometallic Compounds; D003300:Copper; C116609:3-hydroxybutanal
keywords: CC bond cleavage; aldol reaction; asymmetric catalysis; detrifluoroacetylation; fluorinated quaternary stereocenters