70332-63-7

Upstream product

• 614-47-1 1,3-diphenyl-propen-3-one 
• 26553-43-5 cis-2,3-epoxy-1,3-diphenylpropan-1-ol 
• 100-52-7 benzaldehyde 
• 22464-01-3 3-chloro-2-hydroxy-1,3-diphenylpropanone 
• 532-27-4 1-chloroacetophenone 
• 94-41-7 benzalacetophenone 
• 70-11-1 α-bromoacetophenone 
• 19202-21-2 1-trans-cinnamoylpyrrolidine 
• 100-42-5 styrene 
• 98-86-2 acetophenone 
• 591-51-5 phenyllithium 
• 246236-73-7 ((2R,5R)-2,5-Dimethyl-pyrrolidin-1-yl)-((2S,3R)-3-phenyl-oxiranyl)-methanone 
• 246236-74-8 (2S,3R)-3-Phenyl-oxirane-2-carboxylic acid bis-((S)-1-phenyl-ethyl)-amide 
• 108-86-1 bromobenzene 

Downstream Products

• 61762-11-6 (2RS,3SR)-2,3-epoxy-1,1,3-triphenyl-propan-1-ol 
• 94576-67-7 (2RS,3RS)-2-hydroxy-1,3-diphenyl-3-piperidino-propan-1-one 
• 67295-26-5 (2RS,3RS)-2-hydroxy-3-morpholino-1,3-diphenyl-propan-1-one 
• 4927-43-9 5-benzyl-5-phenylimidazolidine-2,4-dione 
• 69897-44-5 trans-(2S,3R)-epoxy-1,3-diphenylpropan-1-one 
• 322-07-6 (RS,RS)-1,3-diphenyl-2-hydroxy-3-fluoropropan-1-one 
• 5381-80-6 anti-1,2-dihydroxy-1,3-diphenylpropane 
• 5381-86-2 (+/-)-(RS,RS)-1,3-diphenyl-1,3-propanediol 
• 22464-01-3 3-chloro-2-hydroxy-1,3-diphenylpropanone 
• 41049-36-9 1-hydroxy-1,3-diphenylacetone 
• 5381-80-6 rac-(1R,2R)-1,3-diphenylpropane-1,2-diol 
• 5381-86-2 (1R,3S)-1,3-diphenylpropane-1,3-diol 
• 42052-51-7 3-hydroxy-1,3-diphenylpropan-1-one 
• 94-41-7 benzalacetophenone 

Relevant academic research and scientific papers

Rate Acceleration of Solid-Liquid Phase-Transfer Catalysis by Rotor-Stator Homogenizer

A rotor-stator homogenizer was found to be an effective mixing tool that accelerated solid-liquid phase-transfer reactions. In the asymmetric alkylation under phase-transfer conditions using the homogenizer, a considerably high turnover frequency was observed. (Figure presented.).

Asymmetric Epoxidation of Enones Promoted by Dinuclear Magnesium Catalyst

Asymmetric synthesis with cheaper and non-toxic alkaline earth metal catalysts is becoming an important and sustainable alternative to conventional catalytic methodologies mostly relying on precious metals. In spite of some sustainable methods for enantioselective epoxidation of enones, the development of a well-defined and efficient catalyst based on magnesium complexes for these reactions is still a challenging task. In this perspective, we present the application of chiral dinuclear magnesium complexes for asymmetric epoxidation of a broad range of electron-deficient enones. We demonstrate that the in situ generated magnesium-ProPhenol complex affords enantioenriched oxiranes in high yields and with excellent enantioselectivities (up to 99% ee). Our extensive study verifies the literature data in this area and provides a step forward to better understand the factors controlling the oxygenation process. Elaborated catalyst offers mild reaction conditions and a truly wide substrate scope. (Figure presented.).

Synthesis of methyl 4,6-di-o-ethyl-α-d-glucopyranoside-based azacrown ethers and their effects in asymmetric reactions

Carbohydrate-based crown ethers have been reported to be able to generate asymmetric induction in certain reactions. Previously, it was proved that the monosaccharide unit, the anomeric substituent, and the sidearm could influence the catalytic activity of the monoaza-15-crown-5 macrocycles derived from sugars. In order to gain information about the effect of the flexibility, 4,6-di-O-ethyl-glucoside-based crown compounds were synthesized, and their efficiency was compared to the 4,6-O-benzylidene analogues. It was found that the absence of the two-ring annulation has a negative effect on the enantioselectivity in liquid-liquid two-phase reactions: in the Darzens condensation of 2-chloroacetophenone and in the epoxidation of chalcone. The same trend was observed in the solid-liquid phase Michael addition of diethyl acetamidomalonate. Surprisingly, in the solid-liquid phase cyclopropanation of benzylidenemalononitrile, one of the new catalysts was highly enantioselective (99% ee).

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

Asymmetric Epoxidation of Olefins Catalyzed by Substituted Aminobenzimidazole Manganese Complexes Derived from L-Proline

A family of manganese complexes [Mn(Rpeb)(OTf)2] (peb=1-(1-ethyl-1H-benzo[d]imidazol-2-yl)-N-((1-((1-ethyl-1H-benzo[d]imidazol-2-yl)methyl) pyrrolidin-2-yl)methyl)-N-methylmethanamine)) derived from L-proline has been synthesized and characterized, where R refers to the group at the diamine backbone. X-ray crystallographic analyses indicate that all the manganese complexes [Mn(Rpeb)(OTf)2] exhibit cis-α topology. These types of complexes are shown to catalyze the asymmetric epoxidation of olefins employing H2O2 as a terminal oxidant with up to 96% ee. Obviously, the R group of the diamine backbone can influence the catalytic activity and enantioselectivity in the asymmetric epoxidation of olefins. In particular, Mn(i-Prpeb)(OTf)2 bearing an isopropyl arm, cannot catalyze the epoxidation reaction with H2O2 as the oxidant. However, when PhI(OAc)2 is used as the oxidant instead, all the manganese complexes including Mn(i-Prpeb)(OTf)2 can promote the epoxidation reactions efficiently. Taken together, these results indicate that isopropyl substitution on the Rpeb ligand inhibits the formation of active Mn(V)-oxo species in the H2O2/carboxylic acid system via an acid-assisted pathway.

Asymmetric epoxidation of α,β-unsaturated ketones via an amine-thiourea dual activation catalysis

A simple asymmetric epoxidation method is developed to effectively synthesize chiral α-carbonyl epoxides through an amine-thiourea dual activation catalysis. In this method, TBHP, as an oxidant, determined the reaction rate, and the chiral amine-thiourea catalyst effectively controlled the stereoselectivity of the reaction, and KOH promoted deprotonation. 22 examples of α,β-unsaturated ketones with various substituent groups are smoothly converted into α-carbonyl epoxides with moderate to excellent enantiomeric excess.

Efficient Aliphatic C-H Oxidation and C═C Epoxidation Catalyzed by Porous Organic Polymer-Supported Single-Site Manganese Catalysts

Bioinspired manganese complexes have emerged over recent decades as attractive catalysts for a number of selective oxidation reactions. However, these catalysts still suffer from oxidative degradation. In the present study, we prepared a series of porous Mn-N4 catalysts in which the catalytic units are embedded in the skeleton of porous organic polymers (POPs). These POP-based manganese catalysts demonstrated high reactivity in the oxidation of aliphatic C-H bonds and the asymmetric epoxidation of olefins. Furthermore, these catalysts could be readily recycled and reused due to their heterogeneous nature. Morphological characterization revealed that the Mn-N4 complex was individually distributed over a porous polymer network. Remarkably, the nature of the single-site catalyst prevented oxidative degradation during the reaction. The present work has thus developed a successful approach for bioinspired single-site manganese catalysts in which the oxidation reaction is confined to a specific channel in an enzyme-like mode.

Synthesis and a Catalytic Study of Diastereomeric Cationic Chiral-at-Cobalt Complexes Based on (R, R)-1,2-Diphenylethylenediamine

Here we report the first synthesis of two diastereomeric cationic octahedral Co(III) complexes based on commercially available (R,R)-1,2-diphenylethylenediamine and salicylaldehyde. Both diastereoisomers with opposite chiralities at the metal center (Λ and Δconfigurations) were prepared. The new Co(III) complexes possessed both acidic hydrogen-bond donating (HBD) NH moieties and nucleophilic counteranions and operate as bifunctional chiral catalysts for the challenging kinetic resolution of terminal and disubstituted epoxides by the reaction with CO2 under mild conditions. The highest selectivity factor (s) of 2.8 for the trans-chalcone epoxide was achieved at low catalyst loading (2 mol %) in chlorobenzene, which is the best achieved result currently for this type of substrate.

Peroxide- And transition metal-free electrochemical synthesis of α,β-epoxy ketones

A novel electrochemical method for the synthesis of α,β-epoxy ketones is reported. With KI as the redox mediator, methyl ketones reacted with aldehydes under peroxide- and transition metal-free electrolytic conditions and afforded α,β-epoxy ketones in one pot (36 examples, 52-90% yield). This safe and environmental-friendly method has a broad substrate scope and can readily provide a variety of α,β-epoxy ketones in gram-scales for evaluation of their anti-cancer activities.

Synthesis of xylal- and arabinal-based crown ethers and their application as asymmetric phase transfer catalysts

New xylal- and arabinal-based monoaza-15-crown-5 ethers were synthesized starting from l- and d-xylose, and l- and d-arabinose, respectively. These monosaccharide-based chiral macrocycles were tested as phase transfer catalysts in a few asymmetric reactions. The xylal-based crown compounds proved to be efficient catalysts in a few liquid-liquid phase reactions. The epoxidation of trans-chalcone and the Darzens condensation of α-chloroacetophenone with benzaldehyde took place with complete diastereoselectivity and up to 77% ee and 58% ee, respectively. It was found that the substituents in the aromatic ring of the chalcone and the α-chloroacetophenone had an influence on the enantioselectivity. The highest ee values were obtained in the epoxidation of 4-chlorochalcone (81% ee) and in the reaction of a 2-naphthyl analogue (96% ee), while in the Darzens condensation of 4-phenyl-α-chloroacetophenone with benzaldehyde, a maximum ee of 91% was detected. The configuration of the monosaccharide unit in the crown ring influenced the absolute configuration of the epoxyketones synthesized.