438631-73-3

Upstream product

• 72758-69-1 (E)-1-(4-bromophenyl)-3-phenylprop-2-en-1-one 
• 2403-27-2 1-(4-bromophenyl)-3-phenyl-2-propen-1-one 
• 100-42-5 styrene 
• 1122-91-4 4-bromo-benzaldehyde 
• 1669-60-9 (E)-1-(4-bromophenyl)-3-phenylprop-2-en-1-ol 
• 99-90-1 para-bromoacetophenone 
• 100-52-7 benzaldehyde 
• 29425-81-8 (4-bromophenyl)(3-phenyloxiran-2-yl)methanone 
• 14531-55-6 3,5-dimethyl-4-nitro-1H-pyrazole 

Relevant academic research and scientific papers

Asymmetric epoxidation of α,β-unsaturated ketones catalyzed by rare-earth metal amides RE[N(SiMe3)2]3with chiral TADDOL ligands

The catalytic asymmetric epoxidation of α,β-unsaturated ketones by tert-butylhydroperoxide (TBHP) has been well established using rare-earth metal amides RE[N(SiMe3)2]3 (RE = La(1), Nd(2), Sm(3), Y(4), Yb(5)) with chiral TADDOL ligands. It was found that

Organocatalytic Enantioselective γ-Elimination: Applications in the Preparation of Chiral Peroxides and Epoxides

An organocatalyzed enantioselective γ-elimination process has been achieved and applied in the kinetic resolution of peroxides to access chiral peroxides and epoxides. The reaction provided a pathway for the preparation of two useful synthetic and biologically important structural motifs through a single-step reaction. A range of substrates has been resolved with a selectivity factor up to 63. The obtained enantioenriched peroxides and epoxides allowed a series of transformations with retained optical purities.

Chiral calcium-catalyzed asymmetric epoxidation reactions using hydrogen peroxide as the terminal oxidant

Asymmetric epoxidation reactions of chalcone derivatives catalyzed by chiral calcium complexes using hydrogen peroxide were developed. The epoxidation reactions proceeded smoothly to afford the desired products in good yields with good enantioselectivitie

Enantioselective Epoxidation of Electron-Deficient Alkenes Catalyzed by Manganese Complexes with Chiral N4 Ligands Derived from Rigid Chiral Diamines

A series of tetradentate sp2N/sp3N hybrid chiral N4 ligands derived from rigid chiral diamines were synthesized, which enabled the first manganese-catalyzed enantioselective epoxidation of electron-deficient alkenes with hydrogen peroxide (H2O2) as an oxidant. The reaction furnishes enantiomerically pure epoxy amides, epoxy ketones as well as epoxy esters in good yields and excellent enantioselectivities (up to 99.9% ee) with lower catalyst loading. Preliminary studies on structure–activity relationship demonstrated that maintaining comparatively lower electron-donating ability of the sp3N and relatively higher electron-donating ability of sp2N of the N4 ligands is beneficial to getting higher activity and selectivity, thus providing us a new view to understand epoxidation with H2O2. (Figure presented.).

Asymmetric synthesis of new γ-butenolides: Via organocatalyzed epoxidation of chalcones

γ-Butenolides have been recognized as an important structural framework in a number of natural products and medicinally important agents. In this work we describe a new metal-free sequential strategy for the asymmetric synthesis of substituted γ-butenolides having epoxychalcones as the advanced intermediate. Using the optimized reaction conditions, we were able to carry out the three-step sequence, epoxidation, olefination and hydrolysis, with only one single chromatographic purification of the final product, furnishing new enantiomerically enriched γ-butenolides in moderate overall yield and good enantiomeric excess.

Asymmetric Epoxidation of Olefins with H2O2 Catalyzed by a Bioinspired Aminopyridine N4 Iron Complex

An iron complex with a chiral aminopyridine N4 ligand bearing strong electron-donating and bulky morpholine groups on the ligand is synthesized and characterized. The iron complex serves to efficiently catalyze the asymmetric epoxidation of various olefins by employing aqueous hydrogen peroxide as the green oxidant, providing the corresponding epoxides in good to excellent yields and enantioselectivities (up to 93 % yield and 99.9 % ee). Owing to the introduction of morpholine functional groups on the ligand, the Fe-catalyzed reaction can proceed with a catalytic amount of the carboxylic acid partner (3 mol %).

Kinetic resolution of 2,3-epoxy 3-aryl ketones via catalytic asymmetric ring-opening with pyrazole derivatives

A highly efficient catalytic kinetic resolution of 2,3-epoxy 3-aryl ketones via asymmetric ring-opening with pyrazole derivatives has been achieved by using a chiral N,N′-dioxide-Sc(III) complex as the catalyst. A wide variety of substrates were readily scoped, and the selectivity factors obtained were excellent (up to >300).

Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Catalyzed by Rare-Earth Amides [(Me3Si)2N]3RE(μ-Cl)Li(THF)3 with Phenoxy-Functionalized Chiral Prolinols

A simple and efficient catalytic enantioselective epoxidation of α,β-unsaturated ketones has been successfully developed, which was catalyzed by rare-earth metal amides [(Me3Si)2N]3RE(μ-Cl)Li(THF)3 (RE = Yb (1), La (2), Sm (3), Y (4), Lu (5)) in the presence of phenoxy-functionalized chiral prolinols at room temperature using tert-butylhydroperoxide (TBHP) as the oxidant. The combination of an Yb-based amide 1 and a chiral proligand (S)-2,4-di-tert-butyl-6-((2-(hydroxydiphenylmethyl)pyrrolidin-1-yl)methyl)phenol) performed very well, and both the yields and the enantiomeric excess of the chiral epoxides reached up to 99% and 99% ee. (Figure Presented).

One-pot production of chiral α,β-epoxy ketones from benzaldehydes and acetophenones by recyclable poly(amino acid) catalysis

An efficient one-pot, two-step process was disclosed for production of chiral α,β-epoxy ketones from benzaldehydes and acetophenones catalyzed by imidazolium-modified poly(l-leucine). Two effective reaction systems with complementary high enantioselectivities (up to 98% ee) or satisfactory yields (up to 89%) have been developed. Importantly, the poly(amino acid) catalyst can be easily recovered and recycled for ten times without losing its catalytic efficiency in terms of both enantioselectivity and yield.

Guanidine-urea bifunctional organocatalyst for asymmetric epoxidation of 1,3-diarylenones with hydrogen peroxide

A highly enantioselective catalytic epoxidation reaction to the electron-deficient α,β-unsaturated olefin moieties of diarylenones was achieved with high chemical yield by using aqueous hydrogen peroxide in the presence of a newly developed guanidine-urea bifunctional organocatalyst. These functional groups were suggested to perform cooperatively by interacting with guanidine-hydrogen peroxide and urea-enones, respectively. Georg Thieme Verlag Stuttgart.