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Asymmetric Synthesis and Application of Chiral Spirosilabiindanes.

Herein, we report the development of a class of chiral spirosilabiindane scaffolds via Rh-catalyzed asymmetric double hydrosilation for the first time. Enantiopure SPSiOL (spirosilabiindane diol), a new type of chiral building block for preparation of various chiral ligands and catalysts, could be readily prepared on >10-gram scale using this protocol. The potential of this new spirosilabiindane scaffold in asymmetric catalysis was preliminarily demonstrated by development of corresponding monodentate phosphoramidite ligands (SPSiPhos), and by applying those ligands in a Rh-catalyzed hydrogenation and a Pd-catalyzed intramolecular carboamination.