Lewis Base‐Catalyzed DYKAT of Racemic Chlorohydrosilanes With Grignard Reagents <i>En</i> Route to <i>Si</i> ‐Stereogenic Hydrosilanes
Abstract
ABSTRACT Enantioenriched hydrosilanes bearing a Si ‐stereogenic center have garnered considerable attention due to the relevance in diverse areas of organic chemistry. Their synthesis has predominantly been limited to stereospecific reduction of chiral silylethers or silazanes, or catalytic desymmetrization of prochiral dihydrosilanes. Herein, we disclose a mechanistically distinct strategy: a ( S , R )‐benzotetramisole‐catalyzed dynamic kinetic asymmetric transformation (DYKAT) of racemic chlorohydrosilanes with Grignard reagents. The method enables enantioconvergent Si*─C bond formation, giving Si ‐stereogenic hydrosilanes—many of which are challenging to access via desymmetrization—in high yields and with high enantioselectivity (34 examples, up to 99% yield, 99:1 er ).
Article Details
Authors (12)
Yulang Tang
Key Laboratory of Drug‐Targeting and Drug Delivery System of the Education Ministry and Sichuan Province Sichuan Engineering Laboratory For Plant‐Sourced Drug West China School of Pharmacy Sichuan University Chengdu China
Qi Zhou
Chongqing University Cancer Hospital Chongqing China
Shuya Li
Tianbao Hu
Yuzhong Kuang
Key Laboratory of Drug‐Targeting and Drug Delivery System of the Education Ministry and Sichuan Province Sichuan Engineering Laboratory For Plant‐Sourced Drug West China School of Pharmacy Sichuan University Chengdu China
Qin Li
Yanqian Xie
Key Laboratory of Drug‐Targeting and Drug Delivery System of the Education Ministry and Sichuan Province Sichuan Engineering Laboratory For Plant‐Sourced Drug West China School of Pharmacy Sichuan University Chengdu China
Mingyuan Yin
Key Laboratory of Drug‐Targeting and Drug Delivery System of the Education Ministry and Sichuan Province Sichuan Engineering Laboratory For Plant‐Sourced Drug West China School of Pharmacy Sichuan University Chengdu China
Lu Gao
Department of Ophthalmology and Visual Science, University of Michigan
Wanshu Wang
Key Laboratory of Drug‐Targeting and Drug Delivery System of the Education Ministry and Sichuan Province Sichuan Engineering Laboratory For Plant‐Sourced Drug West China School of Pharmacy Sichuan University Chengdu China
Zhishan Su
Zhenlei Song
Key Laboratory of Drug‐Targeting and Drug Delivery System of the Education Ministry and Sichuan Province Sichuan Engineering Laboratory For Plant‐Sourced Drug West China School of Pharmacy Sichuan University Chengdu China