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- W3097005181 abstract "Silicon hydrides, alkynylsilanes, and alkoxylsilanes were activated by fluoride in the presence of bisguanidinium catalyst to form hypervalent silicate ion pairs. These activated silicates undergo 1,4-additions with chromones, coumarins, and α-cyanocinnamic esters generating enolsilicate intermediates, for a consequent stereoselective alkylation reaction. The reduction-alkylation reaction proceeded under mild conditions using polymethylhydrosiloxane, a cheap and environmentally friendly hydride source. The addition-alkylation reactions with alkynylsilanes and alkoxylsilanes resulted in the construction of two vicinal chiral carbon centers with excellent enantioselectivities and diastereoselectivities (up to 99% ee, >99:1 dr). Density functional theory calculations and experimental NMR studies revealed that penta-coordinated silicates are crucial intermediates." @default.
- W3097005181 created "2020-11-09" @default.
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- W3097005181 date "2020-10-29" @default.
- W3097005181 modified "2023-10-18" @default.
- W3097005181 title "Enantioselective Addition-Alkylation of α,β-Unsaturated Carbonyls via Bisguanidinium Silicate Ion Pair Catalysis" @default.
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- W3097005181 doi "https://doi.org/10.1021/jacs.0c00183" @default.
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