Enantioselective Dearomatization of Alkylpyridiniums by N‑Heterocyclic Carbene-Catalyzed Nucleophilic Acylation

Enantioselective Dearomatization of Alkylpyridiniums by N‑Heterocyclic Carbene-Catalyzed Nucleophilic Acylation

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...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 83; no. 4; pp. 2050 - 2057
Main Authors: Di Carmine, Graziano, Ragno, Daniele, Bortolini, Olga, Giovannini, Pier Paolo, Mazzanti, Andrea, Massi, Alessandro, Fogagnolo, Marco
Format: Journal Article
Language:English
Published: American Chemical Society 16-02-2018
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Summary: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.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b02996