The synthesis of a new generation of MAP ligands containing two types of chiral elements for asymmetric catalysis

A series of novel aminophosphine ligands containing both axial and central chirality have been synthesized for the first time from NOBIN and tartaric acid derivatives. Their capability for asymmetric induction in the Pd-catalyzed reaction of 1,3-diphenylprop-2-en-1-yl acetate and dimethyl malonate was investigated and the results clearly demonstrated that correct assembly of axial chirality in the scaffold and central chirality of the modification group was very important for achieving higher enantioselectivity in the reaction. In a matched case, the asymmetric allylation product could be obtained in 85.6% ee.