“…Aldol reactions of allenic esters with aldehydes gave the α-hydroxyalkyl allenic esters, whereas functional group tolerance and product yields were unsatisfactory due to the basic reaction conditions . The allenic alcohols bearing an ethoxycarbonyl group at the α-position were provided by the 1,6-cuprate addition to acceptor-substituted enynes followed by the oxidation of titanium enolates with dimethyl dioxirane in a two pot process . Although the allenic alcohols were obtained through the indium-mediated reactions of trialkylsilylpropargyl bromide with aldehydes, the product yields were moderate (45−71%) and the corresponding homopropargylic alcohols were produced as side products .…”
The regio- and chemoselective synthetic method of functionalized alpha-hydroxyalkyl allenic esters was developed from the reactions of various aldehydes with organoindium reagent generated in situ from indium and ethyl 4-bromobutynoate. The alpha-hydroxyalkyl allenic esters possessing electron-donating groups were cyclized to ethyl 2-naphthoate derivatives through intramolecular C-alkylation catalyzed by gold salts.
“…Aldol reactions of allenic esters with aldehydes gave the α-hydroxyalkyl allenic esters, whereas functional group tolerance and product yields were unsatisfactory due to the basic reaction conditions . The allenic alcohols bearing an ethoxycarbonyl group at the α-position were provided by the 1,6-cuprate addition to acceptor-substituted enynes followed by the oxidation of titanium enolates with dimethyl dioxirane in a two pot process . Although the allenic alcohols were obtained through the indium-mediated reactions of trialkylsilylpropargyl bromide with aldehydes, the product yields were moderate (45−71%) and the corresponding homopropargylic alcohols were produced as side products .…”
The regio- and chemoselective synthetic method of functionalized alpha-hydroxyalkyl allenic esters was developed from the reactions of various aldehydes with organoindium reagent generated in situ from indium and ethyl 4-bromobutynoate. The alpha-hydroxyalkyl allenic esters possessing electron-donating groups were cyclized to ethyl 2-naphthoate derivatives through intramolecular C-alkylation catalyzed by gold salts.
“…We have recently proposed a new mechanism for P−C bond formation in Pt-catalyzed hydrophosphination, based on Michael addition of the nucleophilic Pt−PR 2 group to the activated alkene . With mucononitrile, after attack at the cyano-bearing carbon, charge may be delocalized to the other CN group (step a ). , Proton transfer from Pt then yields alkene 5 (step b ). 4 …”
Section: Resultsmentioning
confidence: 99%
“…Soft carbon nucleophiles formed monoadducts with diethylmuconate by attack at the 2-position, but subsequent isomerization gave a mixture of products. See ref , p 648, and references therein.…”
Pt-catalyzed addition of diethylphosphine to the diene
cis,cis-mucononitrile gave the new diphosphine Et2PCH(CN)CH(CH2CH2CN)PEt2 as a 3:2 mixture of diastereomers. Two
monophosphine−alkene intermediates in the hydrophosphination were characterized by NMR spectroscopy.
Introduction
Copper‐Mediated and Copper‐Catalyzed Addition Reactions to Extended Michael Acceptors
Copper‐Mediated and Copper‐Catalyzed Substitution Reactions of Extended Substrates
Conclusion
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