Palladium(0)-catalyzed rearrangement of allyl enol ethers to form chiral quaternary carbon centers via asymmetric allylic alkylation
Sign Up to like & getrecommendations! Published in 2018 at "Tetrahedron Letters"
DOI: 10.1016/j.tetlet.2018.07.065
Abstract: Abstract Herein we report the first palladium(0)-catalyzed asymmetric allylic alkylation (AAA) of allyl enol ether via π -allylpalladium intermediate using Trost chiral diphosphine. This unprecedented reaction produced very rare α-aryl quaternary aldehydes with multi-functional groups.… read more here.
Keywords: enol ethers; allylic alkylation; asymmetric allylic; palladium catalyzed ... See more keywords
Electrochemical, Iodine-Mediated α-CH Amination of Ketones by Umpolung of Silyl Enol Ethers.
Sign Up to like & getrecommendations! Published in 2020 at "Organic letters"
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.
Sign Up to like & getrecommendations! Published in 2021 at "Organic letters"
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
Rhenium-Catalyzed Decarboxylative Coupling of Cyclic Enol Carbonates with Silyl Enol Ethers and Ketene Silyl Acetals.
Sign Up to like & getrecommendations! Published in 2023 at "Organic letters"
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
Sign Up to like & getrecommendations! Published in 2020 at "ACS Catalysis"
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.
Sign Up to like & getrecommendations! Published in 2021 at "Journal of the American Chemical Society"
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
Catalytic Synthesis of 1H-2-Benzoxocins: Cobalt(III)-Carbene Radical Approach to 8-Membered Heterocyclic Enol Ethers.
Sign Up to like & getrecommendations! Published in 2021 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.1c10927
Abstract: The metallo-radical activation of ortho-allylcarbonyl-aryl N-arylsulfonylhydrazones with the paramagnetic cobalt(II) porphyrin catalyst [CoII(TPP)] (TPP = tetraphenylporphyrin) provides an efficient and powerful method for the synthesis of novel 8-membered heterocyclic enol ethers. The synthetic protocol is… read more here.
Keywords: enol ethers; membered heterocyclic; heterocyclic enol; carbene radical ... See more keywords
Formation of Chiral Allylic Ethers via an Enantioselective Palladium-Catalyzed Alkenylation of Acyclic Enol Ethers.
Sign Up to like & getrecommendations! Published in 2018 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.8b02751
Abstract: This report details a palladium-catalyzed process to access highly functionalized, optically active allylic aryl ethers. A number of electron-deficient alkenyl triflates underwent enantioselective and site-selective coupling with acyclic aryl enol ethers in the presence of… read more here.
Keywords: formation chiral; chiral allylic; palladium catalyzed; enol ethers ... See more keywords
Selective synthesis of enol ethers via nickel-catalyzed cross coupling of α-oxy-vinylsulfones with alkylzinc reagents.
Sign Up to like & getrecommendations! Published in 2021 at "Chemical communications"
DOI: 10.1039/d1cc05347g
Abstract: We describe here a Ni-catalyzed Negishi coupling reaction to prepare 1,2-dialkyl enol ethers in a stereoconvergent fashion. This method employs readily available and bench-stable α-oxy-vinylsulfones as electrophiles. The C-sulfone bond in the α-oxy-vinylsulfone motif is… read more here.
Keywords: enol ethers; oxy vinylsulfones; selective synthesis; cross coupling ... See more keywords
Enantioselective Bromination of Silyl Enol Ethers with Chiral Pentacarboxycyclopentadienyl Bromide
Sign Up to like & getrecommendations! Published in 2023 at "Synlett"
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