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.
Design, synthesis and in vitro evaluation against human cancer cells of 5-methyl-5-styryl-2,5-dihydrofuran-2-ones, a new series of goniothalamin analogues
Bruder, Marjorie,Vendramini-Costa, Débora Barbosa,De Carvalho, Jo?o Ernesto,Pilli, Ronaldo Aloise
, p. 5107 - 5117 (2013/09/02)
The present work describes the preparation of a novel series of compounds based on the structure of goniothalamin (1), a natural styryl lactone with known cytotoxic and antiproliferative activities against a variety of cancer cell lines. A focused library of 17 goniothalamin analogues displaying the 5-methyl-2,5-dihydrofuran-2-one motif were prepared, and their cytotoxicity evaluated. While the analogues bearing methoxy and/or hydroxy groups on the aromatic moiety usually were at least three times less potent than the lead compound (1), ortho and para-trifluoromethyl analogues 10 and 11 exhibited levels of cytotoxicity similar to goniothalamin (1) against most cancer cell lines evaluated. One could suggest that the electronic effect of the trifluoromethyl group activates the inhibitor's electrophilic site via reduction of the electron density of the α,β-unsaturated ester oxygen atom. These results provide new information on the structure activity relationship of these α,β-unsaturated styryl lactones, thereby further focusing the design of novel candidates.