Highly enantioselective copper-catalyzed allylic alkylation with atropos phosphoramidites bearing a D2-symmetric biphenyl backbone

A novel class of atropos dibridged biphenyl phosphoramidites bearing a D2-symmetric biphenyl backbone was prepared and applied as chiral ligands in the copper-catalyzed allylic alkylation with Grignard reagent. The alkylation products were obtained in quantitative yields with high regioselectivities up to 94:6 of SN2′/SN2 ratio and enantiomeric excesses up to 91.1% for SN2′ products. The unique D2-symmetric backbone ligands have the advantages of easy preparation and sufficient reusability of their key intermediates from the undesired isomers.

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