Abstract
The asymmetric [4+2] Diels-Alder reaction involving 3,4-dimethyl-1-phenylphosphole, DMPP, as the cyclic diene and its P-sulfonated analogue DMPP S as the dienophile was carried out by utilizing the palladium(II) template complex containing ortho-metalated ( R)-(1-(dimethylamino)ethyl)naphthalene as the chiral auxiliary. The reaction proceeded regiospecifically and stereoselectively to give corresponding phosphanorbornene ▪ ligand as the major product. Throughout the cycloaddition reaction, DMPP functions chemoselectively as the cyclic diene whilst DMPP S assumes the role of dienophile. The absolute stereochemistry of the novel chiral heteroditopic ▪ ligand was established by means of single crystal X-ray diffraction analysis.
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