63473-60-9Relevant articles and documents
ENZYMES IN ORGANIC SYNTHESIS. 42. INVESTIGATION OF THE EFFECTS OF THE ISOZYMAL COMPOSITION OF PIG LIVER ESTERASE ON ITS STEREOSELECTIVITY IN PREPARATIVE-SCALE ESTER HYDROLYSES OF ASYMMETRIC SYNTHETIC VALUE.
Lam,Brown,De Jeso,Lym,Toone,Jones
, p. 4409 - 4411 (1988)
The stereospecificities of the isozyme components of commercially available pig liver esterase have been shown to be essentially the same toward representative monocyclic and acyclic diester substrates. This removes previous concerns that the isozymal com
Cinchona alkaloid derivative modified Fe3O4nanoparticles for enantioselective ring opening of: Meso -cyclic anhydrides
Soni, Hemant P.,Tomer, Sanjiv O.
, p. 2495 - 2507 (2022/02/11)
In the present work, the molecular framework of quinidine was modified at the methoxy functional group of the C6′ carbon of the quinoline moiety with a long-chain carboxylic acid group (-COOH) and it was used as a capping agent during the synthesis of Fe3
Synthesis of a CGRP Receptor Antagonist via an Asymmetric Synthesis of 3-Fluoro-4-aminopiperidine
Molinaro, Carmela,Phillips, Eric M.,Xiang, Bangping,Milczek, Erika,Shevlin, Michael,Balsells, Jaume,Ceglia, Scott,Chen, Jiahui,Chen, Lu,Chen, Qinghao,Fei, Zhongbo,Hoerrner, Scott,Qi, Ji,De Lera Ruiz, Manuel,Tan, Lushi,Wan, Baoqiang,Yin, Jingjun
supporting information, p. 8006 - 8018 (2019/06/17)
A practical and efficient enantioselective synthesis of the calcitonin gene-related peptide receptor antagonist 1 has been developed. The key structural component of the active pharmaceutical ingredient is a syn-1,2-amino-fluoropiperidine 4. Two approaches were developed to synthesize this important pharmacophore. Initially, Ru-catalyzed asymmetric hydrogenation of fluoride-substituted enamide 8 enabled the synthesis of sufficient quantities of compound 1 to support early preclinical studies. Subsequently, a novel, cost-effective route to this intermediate was developed utilizing a dynamic kinetic asymmetric transamination of ketone 9. This synthesis also features a robust Ullmann coupling to install a bis-aryl ether using a soluble Cu(I) catalyst. Finally, an enzymatic desymmetrization of meso-diester 7 was exploited for the construction of the γ-lactam moiety in 1.
Enantioselective acyl-transfer catalysis by fluoride ions
Craig, Ryan,Litvajova, Mili,Cronin, Sarah A.,Connon, Stephen J.
supporting information, p. 10108 - 10111 (2018/09/18)
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.
