A new chiral diphosphine ligand and its asymmetric induction in catalytic hydroformylation of olefins

A new chiral ligand, 1,6-anhydro-2,4-bis(diphenylphosphino)pyranose (ABDPP), was prepared from D-glucose. The ligand was used to prepare a chiral rhodium catalyst system for asymmetric hydroformylation of olefins. For vinyl acetate, the catalytic hydroformylation gave rather high yield (96%), high enantioselectivity (92% eel, and high regioselectivity (b/n = 95/5). But for styrene and norbornene, the results were not so good. The rather high sterioselectivity in the hydroformylation of vinyl acetate is explained in terms of the hydrogen bonding between OH group in the ligand molecule and the carbonyl group of vinyl acetate. (C) 2000 Elsevier Science B.V. All rights reserved.