Enantioselective Hydrolactonization Catalyzed by Chiral Borophosphates
Kuai Yu1,2, Xiangqing Feng1,2, Haifeng Du1,2
1Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
This study introduces a novel metal-free catalytic method for asymmetric hydrolactonization of olefinic carboxylic acids. The new process efficiently synthesizes optically active lactones, creating valuable chiral building blocks for organic synthesis.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Direct asymmetric hydrolactonization of olefinic carboxylic acids is challenging without electrophilic initiators.
- Developing efficient and enantioselective synthetic routes to lactones is crucial in organic chemistry.
Purpose of the Study:
- To develop a novel metal-free catalytic system for the direct asymmetric hydrolactonization of olefinic carboxylic acids.
- To achieve high yields and enantioselectivities in the synthesis of optically active lactones.
Main Methods:
- Utilized an in situ-generated chiral borophosphate as a catalyst.
- Employed olefinic carboxylic acids as substrates.
- Performed the reaction under metal-free conditions.
Main Results:
- Achieved enantioselective, metal-free hydrolactonization of olefinic carboxylic acids.
- Synthesized a variety of optically active lactones in excellent yields.
- Obtained good to high enantioselectivities for the target lactones.
- Successfully constructed lactones with methyl-substituted tertiary stereocenters.
Conclusions:
- The developed protocol offers a facile and efficient approach to enantioselective lactone synthesis.
- The chiral borophosphate catalyst enables metal-free asymmetric hydrolactonization.
- This method provides access to valuable chiral lactone building blocks.
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