13891-95-7Relevant articles and documents
Iridium-catalyzed carbonyl allylation by allyl ethers with tin(II) chloride
Masuyama, Yoshiro,Marukawa, Masanori
, p. 5963 - 5965 (2007)
3-Alkoxypropenes, namely allyl ethers such as allyl butyl ether, allyl 2-hydroxypropyl ether, and diallyl ether, serve as reagents for the allylation of aldehydes with tin(II) chloride in the presence of a catalytic amount of [IrCl(cod)]2 in TH
Gallium metal mediated allylation of carbonyl compounds and imines under solvent-free conditions
Andrews, Philip C.,Peatt, Anna C.,Raston, Colin L.
, p. 243 - 248 (2004)
Gallium metal is effective in mediating the allylation of various carbonyl compounds and imines under solvent-free conditions, with the application of sonic energy, affording the corresponding homoallylic alcohols and amines. The imines themselves were al
Additive effects of ligand activated allylation of aldehydes by allyltrichlorosilane
Short, Joanne D.,Attenoux, Sandrine,Berrisford, David J.
, p. 2351 - 2354 (1997)
The rate of allylation of aldehydes using a combination of allyltrichlorosilane and O-donor ligands can he profoundly accelerated by the addition of a range of simple tetra-n-butylammonium salts. Measured tin values decrease from over 6 hours under define
Ni-Catalyzed 1,2-Diarylation of Alkenyl Ketones: A Comparative Study of Carbonyl-Directed Reaction Systems
Apolinar, Omar,Derosa, Joseph,Engle, Keary M.,Karunananda, Malkanthi K.,Kleinmans, Roman,Li, Zi-Qi,Tran, Van T.,Wisniewski, Steven R.
supporting information, p. 5311 - 5316 (2021/07/26)
A nickel-catalyzed 1,2-diarylation of alkenyl ketones with aryl iodides and arylboronic esters is reported. Ketones with a variety of substituents serve as effective directing groups, offering high levels of regiocontrol. A representative product is diversified into a wide range of useful products that are not readily accessible via existing 1,2-diarylation reactions. Preliminary mechanistic studies shed light on the binding mode of the substrate, and Hammett analysis reveals the effect of electronic factors on initial rates.
Bi(cyclopentyl)diol-Derived Boronates in Highly Enantioselective Chiral Phosphoric Acid-Catalyzed Allylation, Propargylation, and Crotylation of Aldehydes
Yuan, Jinping,Jain, Pankaj,Antilla, Jon C.
, p. 12988 - 13003 (2020/11/23)
In this study, we disclose the catalytic addition of bi(cyclopentyl)diol-derived boronates to aldehydes promoted by chiral phosphoric acids, allowing for the formation of enantioenriched homoallylic, propargylic, and crotylic alcohols (up to >99% enantiom
TetraPh-Tol-BITIOPO: A new atropisomeric 3,3′-bithiophene based phosphine oxide as an organocatalyst in Lewis base-catalyzed Lewis acid mediated reactions
Mirco, Abbinante Vincenzo,Maurizio, Benaglia,Sergio, Rossi,Tiziana, Benincori,Roberto, Cirilli,Marco, Pierini
supporting information, p. 7474 - 7481 (2019/08/20)
A new chiral phosphine oxide based on a 3,3′-bithiophene scaffold (TetraPh-Tol-BITIOPO) was synthesized, fully characterized and separated into antipodes through chiral HPLC. This new compound was successfully employed as an organocatalyst in Lewis base-catalyzed Lewis acid mediated reactions involving trichlorosilyl compounds. The new atropisomeric catalyst was able to promote the allylation of aldehydes with allyltrichlorosilane in up to 98% yield and up to 96% enantiomeric excess (ee), and the direct aldol reaction to afford β-hydroxy ketones and β-hydroxy thioesters, with good chemical yields and modest stereochemical efficiency. Computational studies helped to elucidate and to rationalize the stereochemical outcome of the reactions catalyzed by TetraPh-Tol-BITIOPO that was found to favour the formation of the isomer with an opposite absolute configuration in comparison with the products obtained with the previously reported 3,3′-bithiophene-based catalyst.
