95548-84-8Relevant academic research and scientific papers
The Cyclisation of Secondary Allenic Alcohols
Gallagher, Timothy
, p. 1554 - 1555 (1984)
The silver-mediated cyclisation of secondary allenic alcohols is stereoselective giving predominantly cis-2,6-disubstituted tetrahydropyrans; this methodology has been applied to the synthesis of the civet constituent (4).
Highly active Au(I) catalyst for the intramolecular exo- hydrofunctionalization of allenes with carbon, nitrogen, and oxygen nucleophiles
Zhang, Zhibin,Liu, Cong,Kinder, Robert E.,Han, Xiaoqing,Qian, Hua,Widenhoefer, Ross A.
, p. 9066 - 9073 (2007/10/03)
Reaction of benzyl (2,2-diphenyl-4,5-hexadienyl)carbamate (4) with a catalytic 1:1 mixture of Au[P(t-Bu)2(o-biphenyl)]CI (2) and AgOTf (5 mol %) in dioxane at 25 °C for 45 min led to isolation of benzyl 4,4-diphenyl-2-vinylpyrrolidine-1-carboxylate (5) in 95% yield. The Au(l)-catalyzed intramolecular hydroamination of N-allenyl carbamates tolerated substitution at the alkyl and allenyl carbon atoms and was effective for the formation of piperidine derivatives, γ-Hydroxy and δ-hydroxy allenes also underwent Au-catalyzed intramolecular hydroalkoxylation within minutes at room temperature to form the corresponding oxygen heterocycles in good yield with high exoselectivity. 2-Allenyl indoles underwent Au-catalyzed intramolecular hydroarylation within minutes at room temperature to form 4-vinyl tetrahydrocarbazoles in good yield. Au-catalyzed cyclization of N-allenyl carbamates, allenyl alcohols, and 2-allenyl indoles that possessed an axially chiral allenyl moiety occurred with transfer of chirality from the allenyl moiety to the newly formed stereogenic tetrahedral carbon atom.
SUBSTITUTION REACTIONS OF 2-BENZENESULPHONYL CYCLIC ETHERS WITH CARBON NUCLEOPHILES
Brown, Dearg S.,Bruno, Maurizio,Davenport, Raymond J.,Ley, Steven V.
, p. 4293 - 4308 (2007/10/02)
Direct substitution of 2-benzenesulphonylcyclic ethers was studied using a variety of carbon nucleophiles.These nucleophiles included organozinc reagents (derived from aryl, vinyl and alkynyl Grignard reagents) or silyl enol ethers, silyl ketene acetals,
DIRECT SUBSTITUTION OF 2-BENZENESULPHONYL CYCLIC ETHERS USING ORGANOZINC REAGENTS
Brown, Dearg S.,Ley, Steven V.
, p. 4869 - 4872 (2007/10/02)
2-Benzenesulphonyl cycle ethers are converted in good yield at room temperature to the 2-aryl-, 2-alkenyl or 2-alkynyl product by treatment with the corresponding organozinc species.
