Chiral NHC Ligands Bearing a Pyridine Moiety in Copper-Catalyzed 1,2-Addition of Dialkylzinc Reagents to β‑Aryl-α,β-unsaturated N‑Tosylaldimines

Asymmetric 1,2-addition of dialkylzinc reagents to α,β-unsaturated N-tosylaldimines was catalyzed by copper salt in the presence of chiral imidazolium salts having a pyridine ring, which were derived from amino acid, to afford the corresponding chiral allylic amines with up to 91% ee in reasonably h...

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Veröffentlicht in:Journal of organic chemistry 2016-04, Vol.81 (7), p.2817-2826
Hauptverfasser: Soeta, Takahiro, Ishizaka, Tomohiro, Ukaji, Yutaka
Format: Artikel
Sprache:eng
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Zusammenfassung:Asymmetric 1,2-addition of dialkylzinc reagents to α,β-unsaturated N-tosylaldimines was catalyzed by copper salt in the presence of chiral imidazolium salts having a pyridine ring, which were derived from amino acid, to afford the corresponding chiral allylic amines with up to 91% ee in reasonably high yields. The chiral N-heterocyclic carbene (NHC) ligand played an important role in controlling chemoselectivity.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b00093