39262-22-1Relevant articles and documents
Solid Polymer Electrolytes Comprising Camphor-Derived Chiral Salts for Solid-State Batteries
Armand, Michel,Johansson, Patrik,Lobato, Elias,Martinez-Ibaez, María,Qiao, Lixin,Sanchez-Diez, Eduardo,Santiago, Alexander,Treskow, Marcel,Zhang, Heng,Zhang, Yan
, (2020/10/05)
Solid polymer electrolytes (SPEs) with both excellent processability and flexibility have been deemed as an auspicious alternative to develop safe solid-state lithium metal (Li°) batteries (SSLMBs). The electrochemical performance of SSLMBs is ultimately associated with the nature of the Li-salt anion and the widely used bis(trifluoromethanesulfonyl)imide anion (TFSI) is "slippery"due to its perfluorinated nature and therefore highly mobile, which leads to severe polarization upon battery cell charge/discharge cycles. In this work, we report on a new type of chiral salts, synthesized from commercially available camphorsulfonic acid, used in poly(ethylene oxide) (PEO)-based SPEs. The impact of the chirality of the anions on the fundamental physical properties of the SPEs is extensively studied in terms of thermal stability, phase transition and ionic conductivity, etc. We demonstrate that the resulting SPEs exhibit agreeable ionic conductivities (ca. 104 S cm1) accompanied by high cation transference numbers (ca. 0.5) at 70 °C. Whether either the R or the S enantiomers are used the ion transport properties are the same, as expected, but rather surprisingly the artificial racemic mixture is within the errors of the measurements just as conductive. We discuss how this opens a new avenue to design novel salts for reaching high-performant SSLMBs.
The Ru-catalyzed enantioselective preparation of chiral halohydrins and their application in the synthesis of (R)-clorprenaline and (S)-sotalol
Lu, Chuanjun,Luo, Zonghua,Huang, Ling,Li, Xingshu
experimental part, p. 722 - 727 (2011/08/06)
The asymmetric transfer hydrogenation of a series of halo-substituted aryl methyl ketones, including those substituted in both α-methyl and aryl rings, was studied for the preparation of chiral halohydrins. Up to 99.7% ee was obtained with 2-chloro-1-(2-chlorophenyl)ethanone as the substrate and Ru-CsDPEN as the catalyst in an HCOONa/H2O system. (R)-Clorprenaline, a drug used in the treatment of respiratory disorders, such as bronchitis and asthma, and (S)-sotalol, a class-III antiarrhythmic compound, were prepared with these chiral halohydrins.
A practical large-scale synthesis of (3R,4R)-4-(Hydroxymethyl)pyrrolidin-3- ol via asymmetric 1,3-dipolar cycloaddition
Kotian, Pravin L.,Lin, Tsu-Hsing,El-Kattan, Yahya,Chand, Pooran
, p. 193 - 197 (2012/12/24)
(3R,4R)-4-(Hydroxymethyl)pyrrolidin-3-ol (1), which is a useful intermediate for the synthesis of various bioactive molecules, has been synthesized in 51% overall yield by 1,3-dipolar cycloaddition reaction from the dipolarophile, (E)-3-benzyloxypropenoyl-(2′S)-bornane-10,2-sultam (5), and the achiral ylide precursor, N-(benzyl)-N-(methoxymethyl)-N- (trimethylsilylmethyl)amine (6), without using chromatography and the subsequent reduction with LAH and catalytic hydrogenation. The diastereomers 7 and 8 were separated by crystallization, and efficient procedures were developed for the subsequent reactions to afford 1.
