1. Enantioselective Dearomatization of Alkylpyridiniums by N-Heterocyclic Carbene-Catalyzed Nucleophilic Acylation
- Author
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Daniele Ragno, Olga Bortolini, Pier Paolo Giovannini, Graziano Di Carmine, Alessandro Massi, Marco Fogagnolo, Andrea Mazzanti, Di Carmine, Graziano, Ragno, Daniele, Bortolini, Olga, Giovannini, Pier Paolo, Mazzanti, Andrea, Massi, Alessandro, and Fogagnolo, Marco more...
- Subjects
Organic Chemistry, N-heterocycle Carbenes, Organocatalysis, Asymmetric Synthesis, Dearomatization, 1,4-Dihydropyridine ,Organocatalysis ,010405 organic chemistry ,N-heterocycle Carbenes ,Organic Chemistry ,Enantioselective synthesis ,Ambientale ,Regioselectivity ,010402 general chemistry ,Circular dichroism spectra ,01 natural sciences ,Medicinal chemistry ,0104 chemical sciences ,Catalysis ,Acylation ,Dearomatization ,chemistry.chemical_compound ,chemistry ,Nucleophile ,4-Dihydropyridine ,Carbene ,Asymmetric Synthesis - Abstract
A chiral NHC-catalyzed dearomatizing reaction of activated N-alkylpyridinium salts with aliphatic aldehydes is described. The resulting acylated 1,4-dihydropyridines have been obtained with complete C4 regioselectivity and enantioselectivities in the range 52-78% ee. The (4R)-absolute configuration of the synthesized compounds has been determined by the TD-DFT simulation of the electronic circular dichroism spectra. more...
- Published
- 2018
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