22147-28-0

Upstream product

• 56552-80-8 (R)-3-benzyloxy-1,2-propanediol 
• 105-58-8 Diethyl carbonate 
• 124-38-9 carbon dioxide 
• 14618-80-5 (R)-benzyl glycidol 
• 2930-05-4 Benzyloxymethyl-oxiran 
• 2930-05-4 (S)-benzyl glycidyl ether 
• 949-97-3 4-phenylmethoxymethyl-1,3-dioxolan-2-one 

Downstream Products

• 56552-80-8 (R)-3-benzyloxy-1,2-propanediol 

Relevant academic research and scientific papers

An Aminopyridinium Ionic Liquid: A Simple and Effective Bifunctional Organocatalyst for Carbonate Synthesis from Carbon Dioxide and Epoxides

An aminopyridinium ionic liquid is presented as a green, tunable, and active metal-free one-component catalytic system for the atom-efficient transformation of oxiranes and CO2 to cyclic carbonates. Inclusion of a positively charged moiety into aminopyridines, through a simple single-step synthesis, provides a one-component ionic liquid catalytic system with superior activity; effective in ring opening of epoxide, CO2 inclusion, and stabilization of oxoanionic intermediates. An efficiency assessment of a variety of positively charged aminopyridines was pursued, and the impact of temperature, catalyst loading, and the kind of nucleophile on the catalytic performance was also investigated. Under solvent-free conditions, this bifunctional organocatalytic system was used for the preparation of 18 examples of cyclic carbonates from a broad range of alkyl- and aryl-substituted oxiranes and CO2, where up to 98 percent yield and high selectivity were achieved. DFT calculations validated a mechanism in which nucleophilic ring-opening and CO2 inclusion occur simultaneously towards cyclic carbonate formation.

Bifunctional phase-transfer catalysts for fixation of CO2 with epoxides under ambient pressure

A series of bifunctional phase-transfer catalysts with a quaternary onium center and a hydrogen-bonding donor group were prepared for the fixation of CO2 with commercially available epoxides under mild conditions by using a CO2 balloon (1 atm). In the presence of 2.5 mol% of achiral bifunctional phase-transfer catalysts, cyclic carbonates were obtained in good to excellent yields (up to 95%). Additionally, optical carbonates and epoxides were obtained through the kinetic resolution of rac-epoxides by 1 mol% of chiral bifunctional phase-transfer catalysts with low enantioselectivities. These catalysts featured a simple synthetic route, good modularity and high efficiency.

Chiral Bifunctional Metalloporphyrin Catalysts for Kinetic Resolution of Epoxides with Carbon Dioxide

Chiral binaphthyl-strapped Zn(II) porphyrins with triazolium halide units were synthesized as bifunctional catalysts for kinetic resolution of epoxides with CO2. Several catalysts were screened by changing the linker length and nucleophilic counteranions, and the optimized catalyst accelerated the enantioselective reaction at ambient temperature to produce optically active cyclic carbonates and epoxides.

Efficient and practical organocatalytic system for the synthesis of?cyclic carbonates from carbon dioxide and epoxides: 3-hydroxypyridine/tetra-n-butylammonium iodide

An efficient and practical organocatalytic system comprising 3-hydroxypyridine and tetra-n-butylammonium iodide was developed for the synthesis of cyclic carbonates from carbon dioxide and epoxides under mild conditions (1?atm CO2, 25–60?°C) wi

CO2 Adducts of Phosphorus Ylides: Highly Active Organocatalysts for Carbon Dioxide Transformation

A series of phosphorus ylide (P-ylide) CO2 adducts were synthesized and first used as organocatalysts for CO2 transformation. Detailed studies on the cycloaddition reaction of CO2 with terminal epoxides show that P-ylide CO2 adducts are efficient metal-free and halogen-free organocatalysts to mediate this reaction under ambient conditions (25 °C, 1 atm of CO2). More importantly, the reactions proceeded with a broad scope, high efficiency, and good functional group tolerance and the corresponding cyclic carbonate products were obtained in good to excellent yields (46-99%). Meanwhile, the kinetic study by in situ FTIR methods suggested an intermolecular cooperation effect for effectively accelerating the ring opening of terminal epoxides. Furthermore, from an investigation of the catalytic diversity of P-ylide CO2 adducts, CO2 also could be converted to functionalized cyclic α-alkylidene carbonates, oxazolidinone, and N-methylated and N-formylated amines by organocatalytic reactions.

A single-site hydroxyapatite-bound zinc catalyst for highly efficient chemical fixation of carbon dioxide with epoxides

A zinc-based hydroxyapatite catalyst in conjunction with a Lewis base proved to be efficient for the coupling of CO2 and epoxide in the absence of additional organic solvents under an atmospheric CO2 pressure; the work-up procedure is straight-forward and the catalyst could be reused without loss of catalytic activity and selectivity. The Royal Society of Chemistry 2005.

Enzyme-mediated enantioselective hydrolysis of cyclic carbonates

The enzyme-mediated enantioselective hydrolysis of cyclic carbonates is disclosed. Racemic 4-(2-benzyloxy)ethyl-1,3-dioxolan-2-one (1a) was enantioselectively hydrolyzed by porcine pancreas lipase (PPL) to give optically active (R)-1a and (S)-4-benzyloxybutane-1,2-diol (2a). PPL also catalyzed the hydrolysis of several five-membered cyclic carbonates with high enantioselectivity.

Synthesis of Glyceryletherphosphatides. Preparation of 2-O-Acetyl-1-O--sn-glyceryl-3-phosphorylcholin ('Oleyl PAF'), of its Enantiomer and Some Analogous, Unsaturated Compounds

Syntheses of the unsaturated glyceroletherphospholipid 1a as an olefin-analog of 'Platelet Activating Factor' (PAF) are described together with the methods for the preparation of the enantiomer 1'a, the corresponding 'lyso compounds' 1b and 1'b and their positional isomers 21a, 21'a, 26, 26', 25, 25' obtained on formally exchanging the attachment site of the functional groups at the glycerol moiety.Structural assignments and optical purity of the compounds are confirmed.