60239-39-6Relevant academic research and scientific papers
Tunable Cinchona-Based Thioureas-Catalysed Asymmetric Epoxidation to Synthetically Important Glycidic Ester Derivatives
Meninno, Sara,Zullo, Luca,Overgaard, Jacob,Lattanzi, Alessandra
supporting information, p. 913 - 918 (2017/03/27)
A novel class of synthetically important glycidic esters has been obtained via an asymmetric epoxidation of trans-α-cyano-α,β-unsaturated esters catalysed by a multifunctional Cinchona alkaloid-derived thiourea/tert-butyl hydroperoxide (TBHP) system. The glycidic esters, isolated in excellent yield with complete trans-diastereocontrol and high enantioselectivity, proved to be versatile building blocks to access challenging small targets bearing a quaternary stereocenter. (Figure presented.).
Consecutive oxygen-based oxidations convert amines to α-cyanoepoxides
Ushakov, Dmitry B.,Gilmore, Kerry,Seeberger, Peter H.
supporting information, p. 12649 - 12651 (2015/05/20)
Tri- or tetrasubstituted α-cyanoepoxides can be rapidly prepared from unactivated amines and malononitrile or methyl cyanoacetate when singlet oxygen, produced in a continuous-flow photoreactor, serves as an oxidant and in situ peroxide source. The hydrogen peroxide generated in amine oxidation epoxidizes an electron deficient olefin intermediate, formed by deaminative Mannich coupling. The corresponding α,α-dicyano- or α-cyano-α-esterepoxides were obtained in good yields (43-82%). This journal is
An acidic layered clay is combined with a basic layered clay for one-pot sequential reactions
Motokura, Ken,Fujita, Noriaki,Mori, Kohsuke,Mizugaki, Tomoo,Ebitani, Kohki,Kaneda, Kiyotomi
, p. 9674 - 9675 (2007/10/03)
A Ti4+-exchanged montmorillonite (Ti4+-mont) and a hydrotalcite (HT) are strong solid Bronsted acid and base, and these two clay catalysts could be used in a single reactor without neutralization of active sites. Because the Ti4+-mont have active acid site in the narrow interlayers, the base sites of large HT particles show no interaction with the acid sites. A variety of acid and base reactions, such as esterification, acetalization, deacetalization, aldol reaction, Michael reaction, and epoxidation, proceeded using both the Ti4+-mont and the HT in a single reactor. Copyright
Hydrotalcite-Promoted Epoxidation of Electron-Deficient Alkenes with Hydrogen Peroxide
Cativiela, Carlos,Figueras, Francois,Fraile, Jose M.,Garcia, Jose I.,Mayoral, Jose A.
, p. 4125 - 4128 (2007/10/02)
A synthetic anionic clay, hydrotalcite (Mg/Al=2.8), promotes the epoxidation of electrondeficient alkenes with H2O2.With open-chain, α,β-unsaturated carbonyl compounds 3-hydroxy-1,2-dioxolanes are also obtained.
Synthetic Studies on O-Heterocycles via Cycloadditions. Part 2. Adducts from Styrene Oxides
Clawson, Paul,Lunn, Patricia M.,Whiting, Donald A.
, p. 159 - 162 (2007/10/02)
The styrene oxides (14) and (15), bearing electron-withdrawing functions, readily undergo thermal and photochemical (triplet sensitised) dipolar cycloadditions with simple electron-deficient olefins, regioselectively in the case of methyl acrylate.However, cycloadditions with 5-arylbutenolides as dipolarophiles, required for lignan synthesis, could not be effected in significant yield.A new short route to 5-arylbut-2-enolides was devised.The dihydro- and tetrahydro-furan adducts (18d), (19d), and (20d) all fragment in base to the dienol nitrile (25).
Facile Epoxidation of Alumina-Supported Electrophilic Alkenes and Montmorillonite-Supported Electrophilic Alkenes with Sodium Hypochlorite
Foucaud, Andre,Bakouetila, Medard
, p. 854 - 856 (2007/10/02)
Alkenes gem-substituted by two electron-withdrawing substituents, dispersed on alumina or montmorillonite, are conveniently epoxided by sodium hypochlorite.A mixture of aldehyde and methylcyanoacetate or malononitrile, treated with alumina and sodium hypo
