132015-40-8Relevant articles and documents
Enantioselective acyl-transfer catalysis by fluoride ions
Craig, Ryan,Litvajova, Mili,Cronin, Sarah A.,Connon, Stephen J.
, p. 10108 - 10111 (2018)
The asymmetric nucleophilic catalysis by fluoride ions at a carbon-based electrophile has been demonstrated for the first time. Using a library of ad hoc designed bifunctional phase-transfer catalysts in which both the anion and the cation are directly involved in the reaction, the desymmetrisation of meso-succinic and -glutaric anhydrides is possible.19F NMR spectroscopic studies support the intermediacy of an acyl fluoride intermediate.
Organocatalytic kinetic resolution of racemic secondary nitroallylic alcohols combined with simultaneous desymmetrization of prochiral cyclic anhydrides
Roy, Suparna,Chen, Kan-Fu,Gurubrahamam, Ramani,Chen, Kwunmin
, p. 8955 - 8959 (2014)
This study describes an organocatalytic kinetic resolution of racemic secondary nitroallylic alcohols (2) combined with simultaneous desymmetrization of prochiral cyclic anhydrides (1). The experimental results revealed that enantioselective alcoholysis of 3-substituted glutaric anhydrides afforded hemiesters (3) with high levels of enantioselectivities (up to 99% ee) in the presence of cinchonidine-derived thiourea catalyst (IV). The highly optical enrichment (up to 95% ee) of (S)-nitroallylic alcohols (2) was recovered.
Increased selectivity of novozym 435 in the asymmetric hydrolysis of a substrate with high hydrophobicity through the use of deep eutectic solvents and high substrate concentrations
Fredes, Yerko,Chamorro, Lesly,Cabrera, Zaida
, (2019/03/04)
The effects of the reaction medium and substrate concentration were studied on the selectivity of Novozym 435 using the asymmetric hydrolysis of dimethyl-3-phenylglutarate as a model reaction. Results show that the use of choline chloride ChCl:urea/phosph
Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides
Xu, Lingjun,Han, Shuwen,Yan, Linjie,Wang, Haifeng,Peng, Haihui,Chen, Fener
supporting information, p. 309 - 317 (2018/02/19)
A family of novel chloramphenicol base-amide organocatalysts possessing a NH functionality at C-1 position as monodentate hydrogen bond donor were developed and evaluated for enantioselective organocatalytic alcoholysis of meso-cyclic anhydrides. These structural diversified organocatalysts were found to induce high enantioselectivity in alcoholysis of anhydrides and was successfully applied to the asymmetric synthesis of (S)-GABOB.