Catalytic enantioselective syn hydration of enones in water using a DNA-based catalyst.
The enantioselective addition of water to olefins in an aqueous environment is a common transformation in biological systems, but was beyond the ability of synthetic chemists. Here, we present the first examples of a non-enzymatic catalytic enantioselective hydration of enones, for which we used a catalyst that comprises a copper complex, based on an achiral ligand, non-covalently bound to (deoxy)ribonucleic acid, which is the only source of chirality present under the reaction conditions. The chiral β-hydroxy ketone product was obtained in up to 82% enantiomeric excess. Deuterium-labelling studies demonstrated that the reaction is diastereospecific, with only the syn hydration product formed. So far, this diastereospecific and enantioselective reaction had no equivalent in conventional homogeneous catalysis.
Boersma
Arnold J
AJ
Stratingh Institute for Chemistry and Center for Systems Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
Coquière
David
D
Geerdink
Danny
D
Rosati
Fiora
F
Feringa
Ben L
BL
Roelfes
Gerard
G
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D004247:DNA / Q000737:chemistry*; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry*
D000475:Alkenes; D014867:Water; D004247:DNA