- Nonracemic allylic boronates through enantiotopic-group-selective cross-coupling of geminal bis(boronates) and vinyl halides
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Under the influence of a chiral palladium catalyst, 1,1-bis(pinacolboronate) esters undergo asymmetric cross-coupling with bromoalkenes to generate nonracemic allyl boronates with high levels of enantioselectivity. The so-formed allyl boronates may be oxidized with hydrogen peroxide to provide secondary allylic alcohols or with nitrosobenzene to furnish nonracemic tertiary allylic alcohols. Mechanistic experiments suggest the operation of a pathway involving outer-sphere stereoinvertive transmetalation.
- Potter, Bowman,Szymaniak, Adam A.,Edelstein, Emma K.,Morken, James P.
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Read Online
- An Olefinic 1,2-α-Boryl Migration Enables 1,2-Bis(boronic esters) via Radical-Polar Crossover Reaction
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A radical-induced 1,2-α-boryl migration through radical polar crossover reactions has been described. In this work, in situ formed vinyldiboron “ate” complexes from alkenyl Grignard reagent and diborylalkanes react with commercial radical precursors under light initiation. This three-component process enables diborylation of alkene. This protocol features high atom economy, a broad substrate scope as well as good functional group toleration with mild conditions.
- Zhang, Feng,Liao, Shangteng,Zhou, Lu,Yang, Kai,Wang, Chenglan,Lou, Yixian,Wang, Cece,Song, Qiuling
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p. 582 - 588
(2022/01/11)
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- Reaction Optimization, Scalability, and Mechanistic Insight on the Catalytic Enantioselective Desymmetrization of 1,1-Diborylalkanes via Suzuki-Miyaura Cross-Coupling
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A method for enantioselective desymmetrization of 1,1-diborylalkanes through a stereoselective Pd-catalyzed Suzuki-Miyaura cross-coupling has been thoroughly optimized. The most effective ligand was found to be a α,α,α,α-tetra-aryl-1,3-dioxolane-4,5-dimet
- Sun, Ho-Yan,Kubota, Koji,Hall, Dennis G.
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supporting information
p. 19186 - 19194
(2016/01/25)
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- Synthesis of 1,1-organodiboronates via Rh(I)CI-catalyzed sequential regioselective hydroboration of 1-alkynes
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A Rh(I)Cl-DPPB-complex-catalyzed sequential hydroboration of aryl alkynes and aliphatic alkynes was achieved. The reaction proceeded with almost perfect regioselectivity to afford 1,1-organodiboronate compounds in moderate to good yield. Georg Thieme Verl
- Endo, Kohei,Hirokami, Munenao,Shibata, Takanori
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experimental part
p. 1331 - 1335
(2009/10/23)
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