期刊
NATURE CHEMISTRY
卷 2, 期 11, 页码 991-995出版社
NATURE PUBLISHING GROUP
DOI: 10.1038/NCHEM.819
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资金
- National Research School Combination - Catalysis
- European Research Area Chemistry program
- Netherlands Organisation for Scientific Research
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 beta-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.
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