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Simultaneous Kinetic Resolution and Asymmetric Induction within a Borrowing Hydrogen Cascade Mediated by a Single
Ming Yu Jin1, Yali Zhou1, Dengmengfei Xiao1
1Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055, China.
This study demonstrates a novel borrowing hydrogen cascade reaction. The method achieves kinetic resolution of racemic allylic alcohols and asymmetric synthesis of diverse chiral products with high efficiency and enantioselectivity.
Area of Science:
- Organic Chemistry
- Catalysis
- Stereochemistry
Background:
- Borrowing hydrogen catalysis offers unique mechanistic pathways for cascade reactions.
- Controlling stereochemistry in cascade reactions, including chiral recognition and induction, remains a significant challenge.
Purpose of the Study:
- To develop a borrowing hydrogen cascade reaction for simultaneous kinetic resolution and asymmetric synthesis.
- To explore the conversion of racemic allylic alcohols into various targeted chiral products.
Main Methods:
- Utilized a robust Ruthenium (Ru)-catalyst for the borrowing hydrogen cascade.
- Employed racemic allylic alcohols as starting materials.
- Performed Density Functional Theory (DFT) calculations to understand reaction mechanisms.
Main Results:
- Achieved kinetic resolution of one enantiomer from racemic allylic alcohols.
- Successfully synthesized diverse products, including α,β-unsaturated ketones, β-functionalized ketones, and γ-functionalized alcohols.
- Demonstrated high efficiency and enantioselectivity in both kinetic resolution and asymmetric induction.
Conclusions:
- The developed borrowing hydrogen cascade reaction enables simultaneous kinetic resolution and asymmetric synthesis.
- Catalyst-substrate π-π interactions are crucial for the observed stereochemical diversity, as suggested by DFT calculations.
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