192047-38-4Relevant academic research and scientific papers
Highly efficient enantioselective epoxidation of α,β-enones catalyzed by cheap chiral lanthanum and gadolinium alkoxides
Chen, Ruifang,Qian, Changtao,De Vries, Johannes G
, p. 9837 - 9842 (2001)
(S)-6,6′-Dibromo-BINOL and (S)-6,6′-diphenyl-BINOL have been developed as efficient chiral ligands applicable to lanthanoid catalyzed asymmetric epoxidation of α,β-unsaturated ketones in the presence of cumene hydroperoxide. Excellent chemical yield and e
Scale-up studies for the asymmetric Julia-Colonna epoxidation reaction
Gerlach, Arne,Geller, Thomas
, p. 1247 - 1249 (2004)
The asymmetric Julia-Colonna epoxidation reaction under triphasic/PTC conditions has been successfully scaled-up to a one-hundred gram substrate level providing the corresponding epoxy ketone with high optical purity (up to 97% ee) and in good yield (75-78%). The amount of polyamino acid catalyst could be reduced leading to a simplified reaction work-up. In order to minimise the overall reaction time baffled reactors with pitched-blade impellers have been employed.
Towards a mechanistic insight into the Julia-Colonna asymmetric epoxidation of α,β-unsaturated ketones using discrete lengths of poly- leucine
Bentley, Paul A.,Cappi, Michael W.,Flood, Robert W.,Roberts, Stanley M.,Smith, John A.
, p. 9297 - 9300 (1998)
Accurate length poly-leucines have been used to evaluate mechanistic features of the asymmetric epoxidation of chalcone. Studies have been directed towards the influence of the length of the chain, the stereochemistry of the amino acid residues and the na
Studies in asymmetric epoxidation of chalcone using quaternary salts and nonionic surfactants based on 6-amino-6-deoxy-glucose as chiral phase transfer catalysts
Sharma, Lalit,Sharma, Subhash Chander,Saroj
, p. 1293 - 1297 (2011)
Quaternary salts and nonionic surfactants based on 6-amino-6-deoxy-glucose were explored as chiral phase transfer catalysts for the asymmetric epoxidation of chalcone. Quaternary salts used in the present study, were void of any branched chain or long hyd
Enhanced enantioselectivity in heterogeneous manganese-catalyzed asymmetric epoxidation with nanosheets modified amino acid Schiff bases as ligands by modulating the orientation and the arrangement order
An, Zhe,Han, Hongbo,He, Jing,Jiang, Yitao,Ping, Qi,Shu, Xin,Song, Hongyan,Tang, Yuanzhong,Wang, Wenlong,Xiang, Xu,Zhu, Yanru
, p. 22 - 36 (2021/08/25)
Catalytic enantioselective epoxidation of olefins plays an important role in the production of optically-active epoxy. Transition-metal complexes prove efficient for the catalytic epoxidation of un-functionalized olefins by employing privileged chiral lig
Application of chiral TADDOL ligand and rare earth metal amide in combined catalysis of asymmetric reaction
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Paragraph 0072-0073; 0080-0081, (2020/11/23)
The invention relates to application of chiral TADDOL ligand and rare earth metal amide in combined catalysis of asymmetric epoxidation reaction of chalcone compounds. According to the application, alpha, beta-unsaturated ketone shown in a formula (1) and tert-butyl hydroperoxide react in the presence of organic alkali under the combined catalytic action of a chiral TADDOL ligand shown in a formula (3) and rare earth metal amide in an anhydrous, oxygen-free and protective atmosphere to obtain the chiral epoxy compound shown in the formula (2) after the reaction is completed, wherein R1 is selected from hydrogen, alkyl, halogen, alkoxy, trifluoromethyl, nitro or cyano, R2 is selected from phenyl, substituted phenyl, naphthyl, furyl or thienyl; R3 and R4 are respectively and independently selected from alkyl, phenyl or R3 and R4 and carbon atoms connected with R3 and R4 form naphthenic base; Ar is phenyl, substituted phenyl, biphenyl or naphthyl; the molecular formula of the rare earth metal amide is RE [N (SiMe3) 2] 3. The method has the advantages of wide substrate application range, high yield and high enantioselectivity.
Influence of polymerization degree of poly-l-leucine catalyst and substituent effect on the Julia-Colonna asymmetric epoxidation of benzalacetophenones
Takagi, Ryukichi,Begum, Shahnaz,Siraki, Akiko,Yoneshige, Arata,Koyama, Kin-ichirou,Ohkata, Katsuo
, p. 129 - 141 (2007/10/03)
The Julia-Colonna asymmetric epoxidation reaction of substituted benzalacetophenone afforded the corresponding epoxide with high yield and high enantioselectivity, catalyzed by the specified length of poly-l-leucine (chain length n > 15). Poly-l-leucine catalysts have been prepared by the polymerization reaction of l-leucine-NCA with initiators (BnONa, n-BuNH2, H2O) and characterized by the MALD1-TOF Mass and IR analysis.
Catalytic conversion of conjugated enones into optically active α-keto aziridines using chiral rare earth metal complexes
Sugihara, Hiroyasu,Daikai, Kazuhiro,Jin, Xiu Lan,Furuno, Hiroshi,Inanaga, Junji
, p. 2735 - 2739 (2007/10/03)
Optically active N-unsubstituted α-keto aziridines 2 were synthesized from conjugated enones 1 via the Sc[(R)-BNP]3-catalyzed enantioselective Michael addition of O-methylhydroxylamine followed by the La(O-i-Pr)3-catalyzed ring closu
