- Enantioselective Synthesis of α-Chiral Propargylic Silanes by Copper-Catalyzed 1,4-Selective Addition of Silicon Nucleophiles to Enyne-Type α,β,γ,δ-Unsaturated Acceptors
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A copper-catalyzed deconjugative addition of silicon nucleophiles to a broad range of enyne-type α,β,γ,δ-unsaturated acceptors with high enantiocontrol is reported. The method is 1,4-selective with hardly any formation of the 1,6-adduct. The double-bond geometry is shown to be critical for achieving this chemoselectivity: exclusive 1,4-addition for E and predominant 1,6-addition for Z. By this, E-configured enynoates, enynamides, and enynones have been converted to the corresponding α-chiral propargylic silanes with excellent enantiomeric excesses.
- Mao, Wenbin,Oestreich, Martin
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supporting information
p. 8096 - 8100
(2020/11/02)
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- Chemo- and Regioselective Synthesis of Alkynyl Cyclobutanes by Visible Light Photocatalysis
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Here is the first visible light catalytic intermolecular cross [2 + 2] cycloaddition of enynes with alkenes to alkynyl cyclobutanes established with good functional group tolerance and high reaction efficiency and selectivity. Detailed studies reveal that
- Zhou, Chao,Lei, Tao,Wei, Xiang-Zhu,Liu, Zan,Chen, Bin,Ramamurthy, Vaidhyanathan,Tung, Chen-Ho,Wu, Li-Zhu
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p. 6808 - 6811
(2018/11/21)
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- Gold(I)-catalyzed cycloisomerization of β-alkynylpropiolactones to substituted α-pyrones
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Substituted α-pyrones were straightforwardly synthesized in good to excellent yields by a new gold(I)-catalyzed rearrangement of β-alkynylpropiolactones.
- Dombray, Thomas,Blanc, Aurelien,Weibel, Jean-Marc,Pale, Patrick
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supporting information; experimental part
p. 5362 - 5365
(2011/02/27)
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- A fast and convenient heck reaction in water under microwave irradiation
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A fast and convenient base-free Heck reaction of acrylic acid and allyl alcohol with hypervalent iodonium salts was achieved under microwave irradiation in water, providing a simple method for synthesis of trans-cinnamic acids and trans-cinnamyl alcohols in good yields in short time. Georg Thieme Verlag Stuttgart.
- Zhu, Min,Song, Yunlong,Cao, Yan
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p. 853 - 856
(2008/01/06)
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- Extension of β-chloroenals to ethyl 5-chloro-2,4-pentadienoates using Wadsworth-Emmons reactions: Subsequent conversions to 5-aryl-5-chloro-2,4- pentadienoic acids and 5-aryl-2-penten-4-ynoic acids
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Convenient routes from (Z)-3-aryl-3-chloroenals to (2E,4Z)-5-aryl-5-chloro- 2,4-pentadienoates and (2E)-5-aryl-2-penten-4-ynoates are described. The stereochemical assignments are based on NMR spectral data. Graphical Abstract
- Clough, Stuart C.,Gupton, John T.,Driscoll, David R.,Griffin, Katherine A.,Hewitt, Alisa M.,Hudson, Matthew S.,Ligali, S. Adepeju,Mulcahy, Seann P.,Roberts, Matthew N.,Miller, Robert B.,Belachew, Tsegahiwot T.,Kamenova, Ivanka D.,Kanters, René P.F.,Norwood, Bradley K.
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p. 10165 - 10169
(2007/10/03)
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