Chiral Aziridine Sulfide <i>N(sp3),S</i>-Ligands for Metal-Catalyzed Asymmetric Reactions
Agata J. Pacuła-Miszewska,
Anna Laskowska,
Anna Kmieciak,
Mariola Zielińska-Błajet,
Marek P. Krzemiński,
Jacek Ścianowski
Affiliations
Agata J. Pacuła-Miszewska
Department of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, 7 Gagarin Street, 87-100 Torun, Poland
Anna Laskowska
Department of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, 7 Gagarin Street, 87-100 Torun, Poland
Anna Kmieciak
Department of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, 7 Gagarin Street, 87-100 Torun, Poland
Mariola Zielińska-Błajet
Department of Organic and Medicinal Chemistry, Faculty of Chemistry, Wrocław University of Science and Technology, 27 Wybrzeże Wyspiańskiego Street, 50-370 Wrocław, Poland
Marek P. Krzemiński
Department of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, 7 Gagarin Street, 87-100 Torun, Poland
Jacek Ścianowski
Department of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, 7 Gagarin Street, 87-100 Torun, Poland
A series of new bidentate N,S-ligands—aziridines containing a para-substituted phenyl sulfide group—was synthesized and evaluated in the Pd-catalyzed Tsuji–Trost reaction and addition of diethylzinc and phenylethynylzinc to benzaldehyde. A high enantiomeric ratio for the addition reactions (up to 94.2:5.8) was obtained using the aziridine ligand bearing a p-nitro phenyl sulfide group. Collected results reveal a specific electronic effect that, by the presence of particular electron-donating or electron-withdrawing groups in the PhS- moiety, influences the σ-donor–metal binding and the enantioselectivity of the catalyzed reactions.
