The first example of atropisomeric amide-derived P,O-ligands used for an asymmetric Heck reaction

Atropisomeric N,N-diisopropyl 2-diphenylphosphino- and 2-di(tert-butyl)phosphino-1-naphthamides were used, for the first time, as bidentate P,O-ligands for intermolecular asymmetric Heck reactions of 2,3-dihydrofuran with aryl triflates. The reactions were carried out in the presence of 4 mol% Pd(OAc)2, 8 mol% of the axially chiral ligand, and 3 equiv. of (i-Pr)2NEt in THF at 60 °C for 3 days. Optically active 2-aryl-2,5-dihydrofurans were obtained as the major products along with the rearranged 2-aryl-2,3-dihydrofurans. Enantioselectivity up to 55.2% ee was obtained for the major product.