162405-09-6Relevant articles and documents
Isothiourea-Catalyzed Acylative Kinetic Resolution of Tertiary α-Hydroxy Esters
Greenhalgh, Mark D.,Laina-Martín, Víctor,Neyyappadath, Rifahath M.,Qu, Shen,Smith, Andrew D.,Smith, Samuel M.
supporting information, p. 16572 - 16578 (2020/09/09)
A highly enantioselective isothiourea-catalyzed acylative kinetic resolution (KR) of acyclic tertiary alcohols has been developed. Selectivity factors of up to 200 were achieved for the KR of tertiary alcohols bearing an adjacent ester substituent, with both reaction conversion and enantioselectivity found to be sensitive to the steric and electronic environment at the stereogenic tertiary carbinol centre. For more sterically congested alcohols, the use of a recently-developed isoselenourea catalyst was optimal, with equivalent enantioselectivity but higher conversion achieved in comparison to the isothiourea HyperBTM. Diastereomeric acylation transition state models are proposed to rationalize the origins of enantiodiscrimination in this process. This KR procedure was also translated to a continuous-flow process using a polymer-supported variant of the catalyst.
Facile one-pot preparation of 2-arylpropionic and arylacetic acids from cyanohydrins by treatment with aqueous HI
Aramini, Andrea,Sablone, Manolo R.,Bianchini, Gianluca,Amore, Alessia,Fanì, Michela,Perrone, Plinio,Dolce, Alberto,Allegretti, Marcello
experimental part, p. 2015 - 2021 (2009/07/04)
A novel one-pot two-step procedure has been developed to synthesize highly substituted 2-arylpropionic and arylacetic acids, by treatment with aqueous HI, from cyanohydrins. The hydrogenolytic reduction of α-hydroxy-2-arylpropionic acids was the key step of the process and the optimization of the reaction conditions led to identify aqueous HI as an appropriate and selective reagent for the reductive deoxygenation of cyanohydrins. The synthetic route described a general and efficient strategy for the preparation of large libraries of phenylacetic and phenylpropionic acids derivatives.
Synthesis and properties of 3-alkylsubstituted 1-alkoxy(hydroxy)indolin-2-ones
Geffken,Frobose
, p. 889 - 893 (2007/10/02)
N-alkoxy-2-aryl-2-hydroxycarboxamides 3 are smoothly converted into 3-alkylsubstituted 1-alkoxyindolin-2-ones (2A) by dicyclohexylcarbodiimide in boiling trichloroethene. The acidolysis of the 1-tert-butoxyindolin-2-ones 2Ab, g, i, k as well as the 1-alko