17327-03-6

Upstream product

• 949-97-3 4-phenylmethoxymethyl-1,3-dioxolan-2-one 
• 124-38-9 carbon dioxide 
• 14618-80-5 (R)-benzyl glycidol 
• 2930-05-4 Benzyloxymethyl-oxiran 
• 15028-56-5 4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 13071-59-5 3-benzyloxypropan-1,2-diol 
• 2930-05-4 (S)-benzyl glycidyl ether 

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.

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

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.

Synthesis of Cyclic Organic Carbonates Using Atmospheric Pressure CO2 and Charge-Containing Thiourea Catalysts

Cycloadditions of epoxides with CO2 to synthesize cyclic five-membered ring organic carbonates are of broad interest from a synthetic, environmental, and green chemistry perspective, and the development of effective catalysts for these transformations is an ongoing challenge. A series of eight charge-containing thiourea salts that catalyze these reactions under mild conditions (i.e., 60 °C and atmospheric CO2 pressure) are reported. Substrate scope and mechanistic studies were also carried out, isotope effects were measured, and a reactive intermediate was isolated revealing a surprising pathway in which a thiourea catalyst serves as a nucleophile in the cleavage of the epoxide ring.

An efficient metal- and solvent-free organocatalytic system for chemical fixation of CO2 into cyclic carbonates under mild conditions

An efficient, metal- and solvent-free catalytic system was developed for the conversion of CO2 and epoxides to the corresponding cyclic carbonates under mild conditions (T = 25-45 °C, 1 atm CO2) in high-to-excellent yields. The catal

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.

Preparation of optically active diol derivatives by the enzymatic hydrolysis of cyclic carbonates

A simple enzymatic method for the preparation of optically active 1,2- and 1,3-diol derivatives is disclosed. In the screening of enzymes, 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-(benzyloxy)butane-1,2-diol (2a). The addition of 10% i-PT2O to the reaction system dramatically improved the reactivity to afford optically pure (A)-1a in 31% yield. PPL also catalyzed the hydrolysis of several five-membered cyclic carbonates with high enatioselectivity. It is noteworthy that the increment of the carbon number of the substituents reflects the drastic increase in enantioselectivity. On the other hand, the hydrolyses of six- and seven-membered cyclic carbonates were also catalyzed by PPL. In particular, the reaction of a six-membered substrate enantioselectively proceeded. This reaction afforded optically active 1,3-diol derivatives which could not be directly prepared by hitherto known methods using hydrolytic enzymes.

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.