Enantioselective Synthesis of Planar-Chiral 1,n-Dioxa[n]paracyclophane-Based Phosphites and Their Application as Chiral Ligands

Abstract

Various planar-chiral 1,n-dioxa[n]paracyclophanes possessing a phenolic hydroxyl group have been synthesized via enantioselective ortho-lithiation. Subsequent reaction with 2,2′-biarylene phosphorochloridites gave a new family of chiral phosphites. These phosphites were then used as chiral ligands in the enantioselective palladium-catalyzed allylic alkylation of dimethyl malonate with (E)-1,3-diphenylallyl acetate and the rhodium-catalyzed 1,4-addition of phenylboronic acid to cyclohex-2-enone.

Key words

planar chirality - paracyclophanes - phosphites - chiral ligands - allylic alkylation - 1,4-addition

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