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Updated: Oct 3, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Rhodium hydride enabled enantioselective intermolecular C-H silylation to access acyclic stereogenic Si-H
Kun An1, Wenpeng Ma1, Li-Chuan Liu1
1MOE Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology and School of Pharmaceutical Sciences, Tsinghua University, Beijing, PR China.
Abstract:
The tremendous success of stereogenic carbon compounds has never ceased to inspire researchers to explore the potentials of stereogenic silicon compounds. Intermolecular C-H silylation thus represents the most versatile and straightforward strategy to construct C-Si bonds, however, its enantioselective variant has been scarcely reported to date. Herein we report a protocol that allows for the enantioselective intermolecular C-H bond silylation, leading to the construction of a wide array of acyclic stereogenic Si-H compounds under simple and mild reaction conditions. Key to the success is (1) a substrate design that prevents the self-reaction of prochiral silane and (2) the employment of a more reactive rhodium hydride ([Rh]-H) catalyst as opposed to the commonly used rhodium chloride ([Rh]-Cl) catalyst. This work unveils opportunities in converting simple arenes into value-added stereogenic silicon compounds.
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