Reversible nucleophilic addition can lower the observed enantioselectivity in palladium-catalyzed allylic amination reactions with a variety of chiral ligands was written by Caminiti, Nicholas S.;Goodstein, Madison B.;Leibler, Isabelle N.-M.;Holtzman, Bryan S.;Jia, Zitong B.;Martini, Michael L.;Nelson, Nathaniel C.;Bunt, Richard C.. And the article was included in Tetrahedron Letters in 2015.Application of 174810-09-4 This article mentions the following:
Palladium-catalyzed allylic amination is an important synthetic reaction that is also frequently used as a benchmark for the design and evaluation of new chiral ligands. The effect of reversible nucleophilic addition on the reaction of benzylamine with (E)-1,3-diphenylallyl Et carbonate (1) in CH2Cl2 was examined with 12 different chiral ligands across a range of scaffolding types. In 8 out of 12 cases the observed ee was significantly higher when DBU or Cs2CO3 was added to suppress the proton-driven reversibility. For chiral ligand screening with this test reaction, adding DBU or Cs2CO3 provides a better measure of the ligand’s inherent enantioselectivity. In the experiment, the researchers used many compounds, for example, N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) (cas: 174810-09-4Application of 174810-09-4).
N,N’-((1R,2R)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) (cas: 174810-09-4) belongs to chiral phosphine ligands. Although many reactions require more nucleophilic trialkylphosphines as catalysts, only a few chiral trialkylphosphines are available. Trivalent phosphorus compounds called phosphines have a tetrahedral electron-group geometry which makes them structurally analogous to amines.Application of 174810-09-4
Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis