Enantioselective Construction of Silicon‐Stereogenic Silanes by Scandium‐Catalyzed Intermolecular Alkene Hydrosilylation

Gu Zhan, Huailong Teng, Yong Luo, Shao‐Jie Lou, Masayoshi Nishiura, Zhaomin Hou

Angewandte Chemie International Edition · 2018 · 139 citations · 55 references

Concepts

Abstract

The catalytic asymmetric construction of silicon-stereogenic silanes is of great interest and significance, but has met with only limited success to date. We herein report the enantioselective hydrosilylation of alkenes with dihydrosilanes by a chiral half-sandwich scandium catalyst, which constitutes an efficient and general route for the synthesis of a wide range of enantioenriched silicon-stereogenic silanes from easily accessible starting materials. This reaction features a broad substrate scope, high yields, and high enantioselectivity. Some of the chiral tertiary silane products were also converted into valuable derivatives, such as chiral silanol, quaternary silane, and benzosilole compounds.

References

55