130595-69-6Relevant academic research and scientific papers
Addition of Organochromium Reagents to Aldehydes, Ketones and Enones: a Low-temperature Version of the Nozaki-Hiyama Reaction
Wipf, Peter,Lim, Sungtaek
, p. 1654 - 1656 (1993)
Ph2Cr-tetramethylethylenediamine-mediated Nozaki-Hiyama reaction of allylic and propynylic halides leads to rapid 1,2-addition to aldehydes, ketones and enones at -60 deg C in moderate to high yields.
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.
Synthesis of 1,3-disubstituted cyclohexenes from dienylethers: Via sequential hydrozirconation/deoxygenative cyclisation
Payet, Amandine,Blondeau, Benjamin,Behr, Jean-Bernard,Vasse, Jean-Luc
supporting information, p. 798 - 802 (2019/02/01)
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.
[bmim][Br] as an Inexpensive and Efficient Medium for the Barbier-Type Allylation Reaction Using a Catalytic Amount of Indium: Mechanistic Studies
Dey, Papiya,Koli, Mrunesh,Goswami, Dibakar,Sharma, Anubha,Chattopadhyay, Subrata
, p. 1333 - 1341 (2018/04/02)
Barbier-type allylation reactions of aldehydes and ketones have been carried out with both unsubstituted and γ-substituted allyl bromides using only a catalytic amount (0.1 equiv.) of In metal in [bmim][Br], but not in H2O, organic solvents, or
Base-mediated cascade rearrangements of aryl-substituted diallyl ethers
Reid, Jolene P.,McAdam, Catherine A.,Johnston, Adam J. S.,Grayson, Matthew N.,Goodman, Jonathan M.,Cook, Matthew J.
, p. 1472 - 1498 (2015/02/19)
Two base-mediated cascade rearrangement reactions of diallyl ethers were developed leading to selective [2,3]-Wittig-oxy-Cope and isomerization-Claisen rearrangements. Both diaryl and arylsilyl-substituted 1,3-substituted propenyl substrates were examined, and each exhibits unique reactivity and different reaction pathways. Detailed mechanistic and computational analysis was conducted, which demonstrated that the role of the base and solvent was key to the reactivity and selectivity observed. Crossover experiments also suggest that these reactions proceed with a certain degree of dissociation, and the mechanistic pathway is highly complex with multiple competing routes.
[Bmim] [Br] as a solvent and activator for the ga-mediated barbier allylation: Direct formation of an N -heterocyclic carbene from Ga metal
Goswami, Dibakar,Chattopadhyay, Angshuman,Sharma, Anubha,Chattopadhyay, Subrata
, p. 11064 - 11070 (2013/02/22)
The room-temperature ionic liquid (RTIL) [bmim][Br] has been found to be an excellent green and inexpensive medium for the Ga-mediated allylation of aromatic and aliphatic aldehydes and ketones. The RTIL activated the metal via formation of a Ga-N-heteroc
Mild and general zinc-alkoxide-catalyzed allylations of ketones with allyl pinacol boronates
Fandrick, Keith R.,Fandrick, Daniel R.,Gao, Joe J.,Reeves, Jonathan T.,Tan, Zhulin,Li, Wenjie,Song, Jinhua J.,Lu, Bruce,Yee, Nathan K.,Senanayake, Chris H.
supporting information; experimental part, p. 3748 - 3751 (2010/11/18)
A general and efficient zinc-alkoxide-catalyzed allylation of a diverse array of ketones with allyl boronates is presented. The methodology is effective with 2 mol % of catalyst and with relatively short reaction times. Studies of the key exchange process are presented, which support a cyclic transition state for the boron to zinc exchange.
Solvent effects on the steric course of the [2,3]-wittig rearrangement of (S,E)-[3-(Allyloxy)prop-1-ene-1,3-diyl]dibenzene and derivatives
Ikemoto, Hidaka,Sasaki, Michiko,Takeda, Kei
scheme or table, p. 6643 - 6650 (2011/02/25)
The effect of solvents and additives on the steric course of [2,3]-Wittig rearrangement of the chiral 1,3-diphenyl-1-propenyloxy-2-propen-1-yl carbanion and its derivatives wasexamined on the basis of chirality transfer in intramolecular trapping. Copyrig
In/InCl3-mediated 1,2-addition of allyl group to α,β-unsaturated carbonyl compounds
Kim, Hye Yeon,Choi, Kyung Il,Pae, Ae Nim,Koh, Hun Yeong,Choi, Jung Hoon,Cho, Yong Seo
, p. 1899 - 1904 (2007/10/03)
In/InCl3-mediated addition of allyl iodide to α,β-unsaturated carbonyl compounds gave moderate to high yields of 1,2-addition products. The reactions covered acylic and cyclic α,β-unsaturated carbonyl compounds. Indium trichloride was effective
Ceric(IV) ammonium nitrate: A novel reagent for the synthesis of homoallyl alcohols
Yadav,Reddy,Krishna,Sadasiv,Chary, Ch. Janardhana
, p. 248 - 249 (2007/10/03)
A rapid and highly efficient method has been developed for the allylation of aldehydes with allyltributylstannane using a catalytic amount of eerie ammonium nitrate in acetonitrile under mild and neutral conditions to afford the corresponding homoallyl al
