REACTIVITY OF CHIRAL OXAZAPHOSPHOLIDINES ON ACTIVATED HALIDE COMPOUNDS - SYNTHESIS AND COORDINATION STUDIES OF CHIRAL HYBRID PHOSPHINE-PHOSPHINE OXIDE LIGANDS

The Michaelis Arbuzov reaction between the enantiopure 2-phenyl-1,3,2- oxazaphospholidine 1 and different activated halide compounds 2 afford ed with total diastereoselectivity chiral phosphinamides 3. Oxazaphosp holidine 1 reacted with alpha-haloacetophenones 4a-c to give both chir al Michaelis Arbuzov products 5 and a mixture of diastereomers 6:7 as the Perkow products. New hybrid phosphine-phosphine oxide ligands were easily obtained from phosphinamides 3, bearing chirality on the carbo n chain and the phosphine oxide moiety (BPPO), or on the carbon chain and the two different phosphorus centers (8 and 9). The coordination c hemistry of ligand BPPO has been studied with transition metals and Le wis Acids. (C) 1997 Elsevier Science Ltd.