Carbohydrate-based spiro bis(isoxazolines): synthesis and evaluation in asymmetric catalysis

Two carbohydrate-based spiro bis(isoxazolines) were synthesized and evaluated as ligands for enantioselective reactions in Pd-catalyzed Tsuji-Trost allylic alkylation and Cu(I)-catalyzed alkynylation of imine. While the presence of the palladium caused the rearrangement of the ligand, the Cu(I)-catalysis afforded the desired product in good yield and with modest enantioselectivity.