Axially Chiral N,N-Ligand-Promoted Pd-Catalyzed Enantioselective Allylic Amination and Alkylation

An axially chiral N,N-ligand developed from a [1,1 & PRIME;-binaphthalene]-2,2 & PRIME;-diol(BINOL)-based skeleton and phenanthroline is found to be capable ofpromoting Pd-catalyzed asymmetric allylic amination and alkylationof allyl acetates. The reaction is compatible with cyclic and acyclicsecondary amines, primary aliphatic amines, malononitrile, and dialkylmalonates, affording the corresponding chiral products in up to 99%yield and with up to >99% enantiomeric excess.

Automated summary

An axially chiral N,N-ligand derived from a BINOL-based skeleton and phenanthroline is found to promote Pd-catalyzed asymmetric allylic amination and alkylation of allyl acetates. The reaction is compatible with various amine substrates and affords chiral products with high yield and enantiomeric excess.