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- W1821946364 abstract "A series of nickel-based chiral bifunctional catalysts (1d–3d) with N-heterocyclic carbene (NHC) ligands derived from (1R)-(–)-menthol, (1S)-(–)pinene, and (1R)-(+)-camphor have been successfully designed for asymmetric Michael addition reactions under base-free conditions. The NHC complexes, namely, [1-R-3-{N-(phenylacetamido)}imidazol-2-ylidene]2Ni [R = (1S)-menthyl (1d), (1S)-pinane (2d), and (1R)-isobornyl (3d)], bearing chiral ancillaries on the amido-functionalized side arms of the NHC ligands, performed the bifunctional catalysis of the asymmetric base-free Michael addition reaction of the α-methyl cyano ester substrates ethyl 2-cyanopropanoate (4), isopropyl 2-cyanopropanoate (5), and tert-butyl 2-cyanopropanoate (6) with the activated olefinic substrates methyl vinyl ketone (7) and acrylonitrile (8) in 63–98 % yields with enantiomeric excess (ee) values of 2–75 % at room temperature in 8 h. More interestingly, only the longest of the three catalysts, the menthol derivative 1d, showed significant chiral induction of up to 75 % ee; this has been attributed to the reduction of the steric influence owing to the relatively distant dispositions of the chiral ancillaries from the catalytically active metal center that arise as a consequence of the cis geometries of 1d–3d." @default.
- W1821946364 created "2016-06-24" @default.
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- W1821946364 date "2015-02-16" @default.
- W1821946364 modified "2023-09-26" @default.
- W1821946364 title "Asymmetric Base‐Free Michael Addition at Room Temperature with Nickel‐Based Bifunctional Amido‐Functionalized N‐Heterocyclic Carbene Catalysts" @default.
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- W1821946364 doi "https://doi.org/10.1002/ejic.201403224" @default.
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