Author: "Di Carmine G" / Topic: carbenes - Searchworks@Jio Institute Digital Library Search Results

Author: Brandolese, A., Ragno, D., Leonardi, C., Di Carmine, G., Bortolini, O., De Risi, C., and Massi, A.
Subjects: Organocatalysis, Acylation, Oxidation, Carbenes, Dihydropyrimidines, Acylation, Carbenes, Dihydropyrimidines, Organocatalysis, Oxidation, NO
Published: 2020

Author: Arianna Brandolese, Daniele Ragno, Olga Bortolini, Andrea Mazzanti, Alessandro Massi, Federica Sabuzi, Daniel Pecorari, Graziano Di Carmine, Di Carmine G., Ragno D., Brandolese A., Bortolini O., Pecorari D., Sabuzi F., Mazzanti A., and Massi A.
Subjects: dihydropyridine, DHPS, Oxidative phosphorylation, 010402 general chemistry, 01 natural sciences, Desymmetrization, Catalysis, Settore CHIM/06, NO, desymmetrization, organocatalysis, 010405 organic chemistry, Chemistry, dihydropyridines, Organic Chemistry, Enantioselective synthesis, General Chemistry, density functional calculation, Combinatorial chemistry, 0104 chemical sciences, Quinone, carbene, Organocatalysis, Carbenes, density functional calculations
Abstract: The unprecedented desymmetrization of prochiral dialdehydes catalyzed by N-heterocyclic carbenes under oxidative conditions was applied to the highly enantioselective synthesis of 1,4-dihydropyridines (DHPs) starting from 3,5-dicarbaldehyde substrates. Synthetic elaboration of the resulting 5-formyl-1,4-DHP-3-carboxylates allowed for access to the class of pharmaceutically relevant 1,4-DHP-3,5-dicarboxylates (Hantzsch esters). DFT calculations suggested that the enantioselectivity of the process is determined by the transition state involving the oxidation of the Breslow intermediate by the external quinone oxidant.
Published: 2019

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