title: Diastereomeric resolution of rac-1,1'-bi-2-naphthol boronic acid with a chiral boron ligand and its application to simultaneous synthesis of (R)- and (S)-3,3'-disubstituted 1,1'-bi-2-naphthol derivatives.
abstract: A new concept of diastereomeric resolution has been developed where a boronic acid functionality was employed as (1) a diastereomeric resolving group with a chiral boron ligand and (2) a masked functional group for further transformation thereafter. This new diastereomeric resolution method was successfully applied to the preparation of both (R)- and (S)-3,3'-disubstituted 1,1'-bi-2-naphthol (BINOL) derivatives in a step-ecomonical manner. Racemic BINOL boronic acid reacted with a commercially available pinene-derived iminodiacetic acid as a chiral boron ligand to generate the two diastereomers in quantitative yields over a gram-scale quantity. After the removal of the chiral boron ligand from the diastereomers under mild conditions, the subsequent Suzuki coupling reaction of the resulting chiral BINOL boronic acids with aryl halides provided a series of both (R)- and (S)-BINOL derivatives in good yields. Further, both resulting diastereomers could be directly applied to the Suzuki coupling reaction without the removal of the chiral ligand.
authors.affiliation: Department of Chemistry, Korea University, Anam-ro, Seongbuk-gu, Seoul 136701, Republic of Korea.
authors.forename: Chun-Young
authors.initials: CY
authors.lastname: Lee
authors.forename: Cheol-Hong
authors.initials: CH
authors.lastname: Cheon
mesh_terms: D001896:Boron Compounds / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D009284:Naphthols / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001896:Boron Compounds; D001897:Boronic Acids; D008024:Ligands; D009281:Naphthalenes; D009284:Naphthols; C412332:1,1'-bi-2-naphthol