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.
ASJC Scopus subject areas
- Organic Chemistry