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.
Enantioselective Dearomatization of Alkylpyridiniums by N-Heterocyclic Carbene-Catalyzed Nucleophilic Acylation
Di Carmine, GrazianoPrimo
;Ragno, DanieleSecondo
;Bortolini, Olga;Giovannini, Pier Paolo;Massi, Alessandro
Penultimo
;Fogagnolo, MarcoUltimo
2018
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.File in questo prodotto:
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