title: Phosphoric Acid-Catalyzed Asymmetric Synthesis of SPINOL Derivatives.
abstract: Axially chiral 1,1'-spirobiindane-7,7'-diol (SPINOL) is the most fundamental and important privileged structure from which other chiral ligands containing a 1,1'-spirobiindane backbone are synthesized. Driven by the development of enantioselective syntheses of axially chiral SPINOL derivatives, we have successfully developed the first phosphoric acid-catalyzed asymmetric approach. This approach is highly convergent and functional group tolerant, efficiently providing SPINOLs in good yield with excellent enantioselectivity, thus delivering a practical and straightforward access to this privileged structure. It should be emphasized that the catalyst loading could be decreased to only 0.1 mol% for the preparative-scale synthesis. Furthermore, 4,4'-dimethyl-SPINOL-phosphoric acid was synthesized and applied to catalyze the model reaction for synthesis of enantioenriched SPINOL derivatives.
authors.affiliation: Department of Chemistry, South University of Science and Technology of China , Shenzhen 518055, China.|State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University , Tianjin 300071, China.
authors.forename: Shaoyu
authors.initials: S
authors.lastname: Li
authors.affiliation: Department of Chemistry, South University of Science and Technology of China , Shenzhen 518055, China.
authors.forename: Ji-Wei
authors.initials: JW
authors.lastname: Zhang
authors.affiliation: Department of Chemistry, South University of Science and Technology of China , Shenzhen 518055, China.
authors.forename: Xian-Lin
authors.initials: XL
authors.lastname: Li
authors.affiliation: Department of Chemistry, South University of Science and Technology of China , Shenzhen 518055, China.
authors.forename: Dao-Juan
authors.initials: DJ
authors.lastname: Cheng
authors.affiliation: Department of Chemistry, South University of Science and Technology of China , Shenzhen 518055, China.
authors.forename: Bin
authors.identifier: 0000-0001-8219-9970
authors.initials: B
authors.lastname: Tan