90179-18-3Relevant articles and documents
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
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.
