100840-12-8Relevant articles and documents
Lead-Promoted Allylation of Carbonyl Compounds with Allyl Bromide
Tanaka, Hideo,Yamashita, Shiro,Hamatani, Takeshi,Ikemoto, Youichi,Torii, Sigeru
, p. 1611 - 1614 (1986)
A lead-promoted allylation of carbonyl compounds with allyl bromide in a Pb/Bu4NBr/Me3SiCl/DMF system has been performed in good yields with high chemoselectivities: RCHO > R1R2CO > R1CH(OH)CO2R2 >> R1/sup
Efficient solvent-free synthesis of homoallylic alcohols mediated by zinc-copper couple
Zhou, Wenjun,Yan, Wenjun,Wang, Jin-Xian,Wang, Kehu
, p. 137 - 141 (2008)
Under solvent-free conditions, it was found that zinc-copper couple could efficiently mediate the Barbier-type reaction of ketones and allyl bromide to give the corresponding homoallylic alcohols in high to excellent yields at room temperature. Georg Thieme Verlag Stuttgart.
Indium in Organic Synthesis: Indium-Mediated Allylation of Carbonyl Compounds
Araki, Shuki,Ito, Hirokazu,Butsugan, Yasuo
, p. 1831 - 1833 (1988)
Indium-mediated allylation of a variety of ketones and aldehydes afforded excellent yields of the corresponding homoallylic alcohols under very mild reaction conditions.
Aqueous Reactions with a Lewis Acid and an Organometallic Reagent. The Scandium Trifluoromethanesulfonate-Catalyzed Allylation Reaction of Carbonyl Compounds with Tetraallyltin
Hachiya, Iwao,Kobayashi, Shu
, p. 6958 - 6960 (1993)
The allylation reaction of a wide variety of carbonyl compounds with tetraallyltin was successfully carried out in aqueous media by using scandium trifluoromethanesulfonate (scandium triflate) as a catalyst.
Ligand-accelerated cadmium-catalyzed allylation of aldehydes and ketones in aqueous media
Kobayashi, Shü,Aoyama, Naohiro,Manabe, Kei
, p. 483 - 485 (2002)
Cadmium perchlorate was found to catalyze allylation reactions using allyltributyltin in aqueous media very efficiently. These cadmium-catalyzed allylation reactions are accelerated by ligands such as N,N,N′,N,″N″ -pentamethyldiethylenetriamine or 2,9-dim
Use of π-allylpalladium as a nucleophile via an alkyl-allyl exchange reaction with alkylzinc
Yasui, Kengo,Goto, Youichi,Yajima, Takafumi,Taniseki, Yasue,Fugami, Keigo,Tanaka, Akihiro,Tamaru, Yoshinao
, p. 7619 - 7622 (1993)
Allylation of carbonyl compounds (aldehydes, ketones, esters, lactones, acid anhydrides) proceeds smoothly at room temperature by the reaction of a carbonyl compound, an allylic benzoate or allylic phenyl ether, diethylzinc, and a catalytic amount of Pd(0
Synthesis of 1,3-disubstituted cyclohexenes from dienylethers: Via sequential hydrozirconation/deoxygenative cyclisation
Payet, Amandine,Blondeau, Benjamin,Behr, Jean-Bernard,Vasse, Jean-Luc
, p. 798 - 802 (2019)
Access to 1,3-disubstituted cyclohexenes from zirconocenes containing a latent electrophilic allylic fragment is described. Requiring a specific conformation, 6-endo-trig cyclisation is based on the TMSOTf-mediated generation of a stabilized carbocation.
Tandem Anionic oxy-Cope Rearrangement/Oxygenation Reactions as a Versatile Method for Approaching Diverse Scaffolds
?imek, Michal,Bártová, Kate?ina,Císa?ová, Ivana,Jahn, Ullrich,Pohl, Radek
supporting information, p. 6160 - 6165 (2020/03/03)
Tandem anionic oxy-Cope rearrangement/radical oxygenation reactions provide δ,?-unsaturated α-(aminoxy) carbonyl compounds, which serve as convenient precursors to diverse compound classes. Functionalized carbocycles are accessible by very rare all-carbon 5-endo-trig cyclizations, but also common 5-exo-trig radical cyclizations, based on the persistent radical effect. The tandem reactions can be further extended by highly diastereoselective allylation or reduction steps to give complex scaffolds.
Cooperative titanocene and phosphine catalysis: Accelerated C-X activation for the generation of reactive organometallics
Fleury, Lauren M.,Kosal, Andrew D.,Masters, James T.,Ashfeld, Brandon L.
, p. 253 - 269 (2013/03/14)
The study presented herein describes a reductive transmetalation approach toward the generation of Grignard and organozinc reagents mediated by a titanocene catalyst. This method enables the metalation of functionalized substrates without loss of functional group compatibility. Allyl zinc reagents and allyl, vinyl, and alkyl Grignard reagents were generated in situ and used in the addition to carbonyl substrates to provide the corresponding carbinols in yields up to 99%. It was discovered that phosphine ligands effectively accelerate the reductive transmetalation event to enable the metalation of C-X bonds at temperatures as low as -40 °C. Performing the reactions in the presence of chiral diamines and amino alcohols led to the enantioselective allylation of aldehydes.