- Highly regio- And stereoselective synthesis of cyclic carbonates from biomass-derived polyols: Via organocatalytic cascade reaction
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The cascade reaction of CO2, vicinal diols, and propargylic alcohol, was firstly achieved by dual Lewis base (LB) organocatalytic systems involving LB-CO2 adducts and commercially available organic amines. This methodology could overcome the chemical inertness of CO2, providing an alternative route to various functionalized five-membered cyclic carbonates in moderate to high yields under mild reaction conditions (25 °C, 1.0 atm of CO2). More importantly, this method could also be applied for facile and efficient synthesis of chiral polycyclic carbonates from biomass-derived polyols with complete configuration retention of chiral centers. This study provides an environment-friendly, scalable and cost effective protocol to construct value-added cyclic carbonates with multi-functional groups and chiral centers.
- Zhou, Hui,Zhang, Hui,Mu, Sen,Zhang, Wen-Zhen,Ren, Wei-Min,Lu, Xiao-Bing
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supporting information
p. 6335 - 6341
(2019/12/03)
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- Method for preparing functionalized chiral cyclic carbonate through biomass polyol
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The invention discloses a method for preparing functionalized chiral cyclic carbonate through biomass polyol and belongs to the technical fields of organic synthesis, pesticides, high polymers and medicinal chemical synthesis. The method comprises the step of carrying out a reaction for 1 to 24 hours under the mild condition of 25 DEG C in a manner of taking alpha-methylene cyclic carbonate as a carbonyl source, taking biomass polyol as a reaction substrate and a commercial organic amine as a catalyst, thereby obtaining the functionalized chiral cyclic carbonate. The method has high selectivity, high activity and high functional group tolerance. More importantly, for alditol biomass substrates, which are cheap and readily available and are single in configuration and various in structure,configuration-maintained polycyclic carbonate compounds can be obtained in an efficient and high-selectivity manner. The invention provides an environment-friendly, efficient and convenient synthesisway for developing the functionalized chiral cyclic carbonate.
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Paragraph 0035-0039
(2019/08/12)
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- Intramolecular etherification of five-membered cyclic carbonates bearing hydroxyalkyl groups
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We report a new one-pot synthetic route to tetrahydrofuran derivatives, which were unexpectedly produced under basic conditions by intramolecular etherification of substituted five-membered cyclic carbonates. For alcohols with vicinal hydroxyl groups, and additional OH groups at the β-position, intramolecular etherification leading to 3-hydroxytetrahydrofuran derivatives was observed. These reactions were studied for compounds having from 2 to 6 hydroxyl groups per molecule, and the mechanism was proposed. The developed method provides a new environmentally friendly approach to the synthesis of five-membered cyclic ether derivatives under non-acidic conditions. The Royal Society of Chemistry.
- Tomczyk, Karolina M.,Gunka, Piotr A.,Parzuchowski, Pawel G.,Zachara, Janusz,Rokicki, Gabriel
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p. 1749 - 1758
(2013/02/22)
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