18435-35-3Relevant academic research and scientific papers
Enantioselective synthesis of tertiary and quaternary stereogenic centers: Copper/phosphoramidite-catalyzed allylic alkylation with organolithium reagents
Fananas-Mastral, Martin,Perez, Manuel,Bos, Pieter H.,Rudolph, Alena,Harutyunyan, Syuzanna R.,Feringa, Ben L.
supporting information; experimental part, p. 1922 - 1925 (2012/04/17)
An efficient and highly enantioselective copper-catalyzed allylic alkylation of disubstituted allyl halides with primary and secondary organolithium reagents using phosphoramidite ligands is reported. The use of trisubstituted allyl bromides allows, for the first time, the enantioselective synthesis of all-carbon quaternary stereogenic centers with these reactive organometallic reagents.
γ-Selective allylic substitution reaction with Grignard reagents catalyzed by copper N-heterocyclic carbene complexes and its application to enantioselective synthesis
Tominaga, Satoshi,Oi, Yukinao,Kato, Toshio,An, Duk Keun,Okamoto, Sentaro
, p. 5585 - 5588 (2007/10/03)
The reaction of allylic compounds with alkyl Grignard reagents in the presence of a catalytic amount of copper N-heterocyclic carbene (NHC) complexes proceeded predominantly in an SN2′ reaction pathway to give γ-substituted product in excellent
Synthesis and transformations of metallocycles. 15. A novel method for β-vinylation of α-olefins with AlEt3 under the action of Ni- and Zr-containing catalysts
Ibragimov, A. G.,Zolotarev, A. P.,Muslukhov, R. R.,Lomakina, S. I.,Dzhemilev, U. M.
, p. 113 - 115 (2007/10/02)
A novel regioselective method has been developed for the synthesis of 2-substituted 1,3-butadienes by β-vinylation of α-olefins with AlEt3 in the presence of Ni- and Zr-containing catalysts. - Key words: dienes, synthesis; nickel complexes, catalysts; allyl compounds; organoaluminum compounds.
CROSS-COUPLIN REACTIONS BETWEEN SOME ALLYL, HOMOALLYL, AND HOMOPROPARGYL SUBSTRATES AND TRIALKYLALANES OR DIALKYL- AND DIARYL-MAGNESIUM DERIVATIVES
Tolstikov, G. A.,Dzhemilev, U. M.
, p. 133 - 144 (2007/10/02)
Trialkylalanes and dilkyl- and diaryl-magnesium derivatives can be cross-coupled with allyl ethers and esters, sulphides, and quaternized allylamines.The reactions proceed uncatalyzed either with mild conditions or in the presence of copper complex catalysts to result in high yields of mono- and di-olefins of various structures.The alkylation of homoallyl or homopropargyl tosylates by trialkylalanes is accompanied by cyclization, which leads to alkyl-substituted cyclopropanes. i.e. cyclobutanes and cyclopropylidenes.
Transition-metal-catalysed Grignard Reaction of Secondary Allylic Phosphates
Araki, Shuki,Butsugan, Yasuo
, p. 969 - 972 (2007/10/02)
Regio- and stereo-chemistry of transition-metal-catalysed Grignard reactions of secondary allylic phosphates have been investigated.Best results for regioselective carbon-carbon bond formation at the γ-position of secondary allylic phosphates were attained when copper(I) iodide was used as the catalyst.The naturally occuring monoterpene alcohols, geraniol and the sex pheromone of the African Monarch, were synthesized as a demonstration of the synthetic utility of the newly developed coupling reaction.
SYNTHESE A L'AIDE DE SULFONE-XXV. SUBSTITUTION SUR DES SULFONES: L'ANION PHENYLSULFINATE COMME GROUPE PARTANT DANS LA SUBSTITUTION DES SULFONES ALLYLIQUES PAR DES REACTIFS DE GRIGNARD EN PRESENCE DE SELS DE CUIVRE
Julia, Marc,Righini-Tapie, Anne,Verpeaux, Jean-Noel
, p. 3283 - 3288 (2007/10/02)
Displacement reactions of the sulphinate anion from sulfones by Grignard reagents with copper catalysis take place readily with allylic sulphones.The regio chemistry and stereochemistry of the reaction are discussed.
