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Keywords = Hosomi-Sakurai allylation

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10 pages, 5997 KiB  
Article
Trityl Cation-Catalyzed Hosomi-Sakurai Reaction of Allylsilane with β,γ-Unsaturated α-Ketoester to Form γ,γ-Disubstituted α-Ketoesters
by Zubao Gan, Deyun Cui, Hongyun Zhang, Ying Feng, Liying Huang, Yingying Gui, Lu Gao and Zhenlei Song
Molecules 2022, 27(15), 4730; https://doi.org/10.3390/molecules27154730 - 24 Jul 2022
Cited by 3 | Viewed by 2620
Abstract
(Ph3C)[BPh(F)4]-catalyzed Hosomi-Sakurai allylation of allylsilanes with β,γ-unsaturated α-ketoesters has been developed to give γ,γ-disubstituted α-ketoesters in high yields with excellent chemoselectivity. Preliminary mechanistic studies suggest that trityl cation dominates the catalysis, while the silyl cation plays a minor role. Full article
(This article belongs to the Special Issue Chemical Synthesis of Natural Products)
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9 pages, 2415 KiB  
Article
Steps toward Rationalization of the Enantiomeric Excess of the Sakurai–Hosomi–Denmark Allylation Catalyzed by Biisoquinoline N,N’-Dioxides Using Computations
by Pierpaolo Morgante, Coty Deluca, Tegla E. Jones, Gregory J. Aldrich, Norito Takenaka and Roberto Peverati
Catalysts 2021, 11(12), 1487; https://doi.org/10.3390/catal11121487 - 4 Dec 2021
Viewed by 2906
Abstract
Allylation reactions of aldehydes are chemical transformations of fundamental interest, as they give direct access to chiral homoallylic alcohols. In this work, we focus on the full computational characterization of the catalytic activity of substituted biisoquinoline-N,N’-dioxides for the allylation of 2-naphthaldehyde. We characterized [...] Read more.
Allylation reactions of aldehydes are chemical transformations of fundamental interest, as they give direct access to chiral homoallylic alcohols. In this work, we focus on the full computational characterization of the catalytic activity of substituted biisoquinoline-N,N’-dioxides for the allylation of 2-naphthaldehyde. We characterized the structure of all transition states as well as identified the π stacking interactions that are responsible for their relative energies. Motivated by disagreement with the experimental results, we also performed an assessment of 34 different density functional methods, with the goal of assessing DFT as a general tool for understanding this chemistry. We found that the DFT results are generally consistent as long as functionals that correctly account for dispersion interactions are used. However, agreement with the experimental results is not always guaranteed. We suggest the need for a careful synergy between computations and experiments to correctly interpret the data and use them as a design tool for new and improved asymmetric catalysts. Full article
(This article belongs to the Special Issue Heteroaromatic N-oxides in Synthesis and Asymmetric Catalysis)
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