Asymmetric Synthesis and Application of Chiral Spirosilabiindanes
Xin Chang, Pei‐Long Ma, Hong‐Chao Chen, Chuan‐Ying Li, Peng Wang
Abstract
Abstract Reported here is the development of a class of chiral spirosilabiindane scaffolds by Rh‐catalyzed asymmetric double hydrosilation, for the first time. Enantiopure SPSiOL (spirosilabiindane diol), a new type of chiral building block for the preparation of various chiral ligands and catalysts, was readily prepared on greater than 10 gram scale using this protocol. The potential of this new spirosilabiindane scaffold in asymmetric catalysis was preliminarily demonstrated by development of the corresponding monodentate phosphoramidite ligands (SPSiPhos), which were used in both a Rh‐catalyzed hydrogenation and a Pd‐catalyzed intramolecular carboamination.
Topics & Concepts
Enantiopure drugPhosphoramiditeChemistryEnantioselective synthesisCatalysisIntramolecular forceDenticityCombinatorial chemistryAsymmetric hydrogenationStereochemistryOrganic chemistryCrystal structureOligonucleotideDNABiochemistryAsymmetric Hydrogenation and CatalysisOrganometallic Complex Synthesis and CatalysisCatalytic C–H Functionalization Methods