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Beilstein J. Org. Chem. 2016, 12, 1185–1195, doi:10.3762/bjoc.12.114
Graphical Abstract
Figure 1: Structural motifs of phospinooxazoline ligands.
Scheme 1: Retrosynthetic analysis for NeoPHOX ligands.
Scheme 2: Synthesis of 1st generation NeoPHOX Ir-complexes [19].
Figure 2: Asymmetric hydrogenation with iridium-NeoPHOX catalysts [19].
Figure 3: Employing L-valine as a starting material for C5 substituted oxazoline.
Scheme 3: Synthesis of a C(5)-disubstituted NeoPHOX-Ir complex.
Figure 4: Retrosynthetic analysis for NeoPHOX ligands derived from serine and threonine.
Scheme 4: Revisited synthetic strategy for the preparation of a threonine-based NeoPHOX ligand.
Scheme 5: Undesired β-lactam formation.
Scheme 6: Synthetic strategy for the synthesis of the serine-derived NeoPHOX ligand.
Scheme 7: Derivatization of the 2nd generation NeoPHOX ligands and formation of their iridium complexes.
Figure 5: Crystal structures of selected Ir-complexes. Hydrogen atoms, COD and BArF anions were omitted for c...
Scheme 8: Asymmetric palladium-catalyzed allylic substitution with rac-(E)-1,3-diphenylallyl acetate.
Scheme 9: Asymmetric palladium-catalyzed allylic substitution with rac-(E)-1,3-dimethylallyl acetate.
Scheme 10: Asymmetric palladium-catalyzed allylic substitution with a cyclic substrate.