NOBIN-based chiral phosphite-type ligands and their application in asymmetric catalysis. Issue 33 (12th August 2015)

• Record Type: Journal Article
• Authors: Gavrilov, Konstantin N.; Shiryaev, Alexei A.; Zheglov, Sergey V.; Bochelyuk, Marina S.; Chuchelkin, Ilya V.; Tafeenko, Viktor A.; Chernyshev, Vladimir V.; Zamilatskov, Ilya A.; Mikhel, Igor S.
• Is Part Of: Tetrahedron letters. Volume 56:Issue 33(2015)
• Page Start: 4756
• Page End: 4761
• Publication Date: 2015-08-12
• Subjects: Asymmetric allylic substitution -- Palladium -- Asymmetric conjugate addition -- Copper -- Phosphorus ligands; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.06.047
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: P ∗ -Monodentate diamidophosphite and diastereomeric P, N -containing phosphite ligands have been synthesized from enantiomerically pure N -Bn-NOBIN and used as asymmetric inductors in Pd-catalyzed allylic substitution and Cu-catalyzed conjugate addition reactions. The best results (up to 93% ee) were obtained for the Pd-catalyzed allylic alkylation of ( E )-1, 3-diphenylallyl acetate with 1-cyclohexenylpyrrolidine. The reactions of P, N -containing ligands with Pd(COD)Cl2 at molar ratios of L/M = 1 and 2 were studied using 1 H, 13 C, and 31 P NMR spectroscopy as well as HRESI mass spectrometry, showing the trans -PdCl2 L2 complex was the only product.