Electrochemical, Iodine-Mediated α-CH Amination of Ketones by Umpolung of Silyl Enol Ethers.
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DOI: 10.1021/acs.orglett.0c02068
Abstract: The electrochemical, oxidative Umpolung reaction of silyl enol ethers utilizing simple iodide salts for the synthesis of α-amino ketones is described. The products were isolated in excellent yields of up to 100%, and various functionalized… read more here.
Keywords: silyl enol; electrochemical iodine; enol ethers; mediated amination ... See more keywords
Rhodium-Catalyzed β-Dehydroborylation of Silyl Enol Ethers: Access to Highly Functionalized Enolates.
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DOI: 10.1021/acs.orglett.1c03796
Abstract: An efficient rhodium-catalyzed β-dehydroborylation of aldehyde-derived silyl enol ethers (SEEs) with bis(pinacolato)diboron (B2pin2) is disclosed. The borylation reactions proceeded well with alkyl- and aryl-substituted SEEs, affording a wide array of valuable functionalized β-boryl silyl enolates… read more here.
Keywords: silyl enol; catalyzed dehydroborylation; enol ethers; rhodium catalyzed ... See more keywords
Oxygenated Cyclopentenones via the Pauson–Khand Reaction of Silyl Enol Ether Substrates
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DOI: 10.1021/acs.orglett.2c00856
Abstract: We report here the application of silyl enol ether moieties as efficient alkene coupling partners within cobalt-mediated intramolecular Pauson–Khand reactions. This cyclization strategy delivers synthetically valuable oxygenated cyclopentenone products in yields of ≤93% from both… read more here.
Keywords: enol ether; pauson khand; oxygenated cyclopentenones; silyl enol ... See more keywords
Rhenium-Catalyzed Decarboxylative Coupling of Cyclic Enol Carbonates with Silyl Enol Ethers and Ketene Silyl Acetals.
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DOI: 10.1021/acs.orglett.3c00543
Abstract: The Lewis acid-catalyzed decarboxylative coupling of cyclic enol carbonates, prepared by the fixation of carbon dioxide onto propargyl alcohols, with silyl enol ethers including ketene silyl acetals, was developed to afford 1,4-dicarbonyl compounds in good-to-high… read more here.
Keywords: coupling cyclic; silyl enol; catalyzed decarboxylative; decarboxylative coupling ... See more keywords
Fluoride Anions in Self-Assembled Chiral Cage for the Enantioselective Protonation of Silyl Enol Ethers.
Sign Up to like & getrecommendations! Published in 2017 at "Organic letters"
DOI: 10.1021/acs.orglett.7b01429
Abstract: The potential of Song's chiral oligoethylene glycols (oligoEGs) as catalysts was explored in the enantioselective protonation of trimethylsilyl enol ethers in combination with alkali metal fluoride (KF and CsF) and in the presence of a… read more here.
Keywords: silyl enol; enol ethers; enantioselective protonation; enol ... See more keywords
α-Arylation of Silyl Enol Ethers via Rhodium(III)-Catalyzed C–H Functionalization
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DOI: 10.1021/acscatal.9b05622
Abstract: Carbon–hydrogen (C–H) bond functionalization streamlines synthesis by increasing step- and atom-economies. This approach, catalyzed by Rh(III), is combined with the α-arylation of ketone-derived si... read more here.
Keywords: iii; silyl enol; enol ethers; arylation silyl ... See more keywords
Enantioselective Rh-Catalyzed Hydroboration of Silyl Enol Ethers.
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DOI: 10.1021/jacs.1c06697
Abstract: The asymmetric hydroboration of alkenes has proven to be among the most powerful methods for the synthesis of chiral boron compounds. This protocol is well suitable for activated alkenes such as vinylarenes and alkenes bearing… read more here.
Keywords: enol ethers; silyl enol; hydroboration silyl; hydroboration ... See more keywords
Enantioselective Bromination of Silyl Enol Ethers with Chiral Pentacarboxycyclopentadienyl Bromide
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DOI: 10.1055/a-2088-9219
Abstract: Chiral pentacarboxycyclopentadienyl bromide reagents were synthesized to accomplish enantioselective bromination of silyl enol ethers to give corresponding α-bromoketone products in good yields and up to 77% ee. A catalytic version of this reaction was also… read more here.
Keywords: chiral pentacarboxycyclopentadienyl; silyl enol; pentacarboxycyclopentadienyl bromide; enantioselective bromination ... See more keywords