52129-50-7Relevant academic research and scientific papers
A General Allylation Procedure Using Trimethylallylsilane and Fluoride Catalysis
Majetich, George,Casares, Ada,Chapman, David,Behnke, Mark
, p. 1745 - 1753 (1986)
The relative effectiveness for conjugate addition of lithium diallylcuprate, Lewis acid catalyzed addition of trimethylallylsilane, and fluoride ion catalyzed addition of trimethylallylsilane was compared by using a variety of Michael acceptors of differi
Additive Tuned Selective Synthesis of Bicyclo[3.3.0]octan-1-ols and Bicyclo[3.1.0]hexan-1-ols Mediated by AllylSmBr
Wang, Xiaoxia,Li, Jianyong,Yuan, Ting,You, Bingxin,Xie, Guanqun,Lv, Xin
, p. 8984 - 8994 (2018/07/05)
The selective construction of bicyclo[3.3.0]octan-1-ols and bicyclo[3.1.0]hexan-1-ols was achieved by using an allylSmBr/additive(s) system. By employing HMPA as the only additive, the momoallylation/ketone-alkene coupling occurred preferably and afforded bicyclo[3.3.0]octan-1-ols in good yields with high diastereoselectivities. While the ester-alkene coupling predominated to generate bicyclo[3.1.0]hexan-1-ols in moderate yields with excellent diastereoselectivities in the presence of a proton source, such as pyrrole as the coadditive with HMPA. The tunable reactivity of allylSmBr by additive(s) would make it a versatile reagent in organic synthesis.
Sc(OTf)3-catalyzed conjugate allylation of alkylidene meldrum's acids
Dumas, Aaron M.,Fillion, Eric
supporting information; experimental part, p. 1919 - 1922 (2009/09/25)
Alkylidene Meldrum's acids are allylated in a conjugate fashion by allyltin nucleophiles under mild Sc(OTf)3-catalyzed conditions. The addition is functional group tolerant and reactions with nonracemic alkylidenes are highly diastereoselective
Diastereoselective intermolecular cyclopropanation of simple alkenes by fischer alkenyl and heteroaryl carbene complexes of chromium: Scope and limitations
Barluenga, Jose,Lopez, Salome,Trabanco, Andres A.,Fernandez-Acebes, Alvaro,Florez, Josefa
, p. 8145 - 8154 (2007/10/03)
The intermolecular cyclopropanation of simple alkyl-substituted alkenes with Fischer methoxycarbene complexes under thermal conditions is reported. The scope and limitations of this [2 + 1] cycloaddition with respect to the nature of the carbene complex,
Stereocontrol in the intramolecular Buchner reaction of diazoketones
Maguire, Anita R.,Buckley, N. Rachael,O'Leary, Patrick,Ferguson, George
, p. 4077 - 4091 (2007/10/03)
Rhodium(II) acetate catalysed intramolecular Buchner cyclisation of a series of diazoketones 1 proceeds with excellent diastereoselectivity to produce the trans substituted azulenones 2, which exist as a rapidly equilibrating cycloheptatriene-norcaradiene system, from which the norcaradiene tautomers can be efficiently trapped as PTAD cycloadducts 4. The cyclisation-cycloaddition sequence can be conducted in either a stepwise or a tandem process, leading to the pentacyclic systems 4 as a single diastereomer in each case. In the reaction of diazoketone If intramolecular cyclopropanation competes with cyclisation to the aromatic ring.
Preparation and Reactivities of (η3-1- and 2-Trimethylsiloxyallyl)Fe(CO2)NO Complexes. Intermediates Functioning as Equivalents of β- and α-Acyl Carbocations and Acyl Carbanions
Itoh, Keiji,Nakanishi, Saburo,Otsuji, Yoshio
, p. 2965 - 2977 (2007/10/02)
(η3-1- and 2-Trimethylsiloxyallyl)Fe(CO)2NO complexes were prepared by the reaction of the corresponding siloxyallylic halides with Bu4N.These complexes reacted with both of carbon nucleophiles and carbon electrophiles preferentially at the less hindered sites of the allylic ligands.In these reactions, (η3-1-trimethylsiloxyallyl)Fe(CO)2NO complexes served as synthetically equivalent synthons for both of β-acyl carbocations and β-acyl carbanions and (η3-2-trimethylsiloxyallyl)Fe(CO)2NO complexes as both of α-acyl carbocations and α-acyl carbanions.The stereochemical courses of the reactions are described.
Addition diastereoselective d'allyl cuprates a des imides chirales insaturees
Pourcelot, G.,Melnyk, O.,Besace, Y.,Stephan, E.,Cresson, P.
, p. C5 - C8 (2007/10/02)
Magnesium diallyl cuprate will add to unsaturated imides, synthesized from chiral imidazolidinones, with very high diastereoselectivity and good yields.Isoprenyl cuprate gives addition with lower yield and stereoselectivity.The products show total allylic inversion.
Electrochemical Coupling of Activated Olefins and Alkyl Dihalides: Formation of Cyclic Compounds
Lu, Yu-Wei,Nedelec, Jean-Yves,Folest, Jean-Claude,Perichon, Jacques
, p. 2503 - 2507 (2007/10/02)
The electrochemical coupling of dimethyl maleate, methyl cinnamate, 4-phenyl-3-buten-2-one, or methyl acrylate with dibromomethane, 1,3-dibromopropane, 1,4-dibromobutane or other substituted alkyl dihalogenides gave satisfactory yields of cyclic products.The reactions were performed in an undivided cell fitted with a sacrificial aluminum anode, in N-methylpyrrolidone (NMP), at constant current, and at room temperature.The role of the anodically generated metallic ions in this cyclocondensation has been evidenced.
3-Substituted-γ-butyrolactones from 5-Trimethylsilyl-2-cyclohexenone. Synthesis of (-)-Enterolactone
Asaoka, Morio,Fujii, Naoaki,Shima, Kunihisa,Takei, Hisashi
, p. 805 - 808 (2007/10/02)
1,4-Adducts of 5-trimethylsilyl-2-cyclohexenone (1) with Grignard reagents were converted to various hexanoate derivatives and γ-butyrolactones.Starting from optically pure 1, (-)-enterolactone (Factor X) was synthesized.
CHEMOSELECTIVITY IN THE CONJUGATE ADDITION OF ALLYLSILANE TO MICHAEL ACCEPTORS
Majetich, George,Casares, Ada M.,Chapman, D.,Behnke, M.
, p. 1909 - 1912 (2007/10/02)
The allylic carbanion species generated by treatment of allylsilane with fluoride ion undergoes highly chemoselective conjugate addition to a series of Michael acceptors for which alternative known allylation procedures proved less general.
