Enantioselective Hydrolactonization Catalyzed by Chiral Borophosphates

The direct asymmetric hydrolactonization of olefinic carboxylic acids without the aid of electrophilic initiators remains a significant challenge in synthetic chemistry. Herein, we report an enantioselective, metal-free hydrolactonization of olefinic carboxylic acids utilizing an <i>in situ</i>-generated chiral borophosphate as the catalyst. A variety of optically active lactones were obtained in excellent yields with good to high enantioselectivities. This protocol provides a facile and efficient approach to the construction of lactones bearing methyl-substituted tertiary stereocenters.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-01-15
DOI
https://doi.org/10.1021/acs.joc.5c02774
Citations
2
Primary Topic
Organoboron and organosilicon chemistry
Type
article
Field-Weighted Citation Impact
45.90
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article

Enantioselective Hydrolactonization Catalyzed by Chiral Borophosphates

Xiaoming Feng, Haifeng Du, Kuai Yu
2 citations
The Journal of Organic Chemistry
Organoboron and organosilicon chemistry
45.90
article

Enantioselective Hydrolactonization Catalyzed by Chiral Borophosphates

Xiaoming Feng, Haifeng Du, Kuai Yu
article en
2 citations

Abstract

The direct asymmetric hydrolactonization of olefinic carboxylic acids without the aid of electrophilic initiators remains a significant challenge in synthetic chemistry. Herein, we report an enantioselective, metal-free hydrolactonization of olefinic carboxylic acids utilizing an <i>in situ</i>-generated chiral borophosphate as the catalyst. A variety of optically active lactones were obtained in excellent yields with good to high enantioselectivities. This protocol provides a facile and efficient approach to the construction of lactones bearing methyl-substituted tertiary stereocenters.

The Journal of Organic ChemistryVol. 91(4)
Chinese Academy of Sciences (CN), Beijing National Laboratory for Molecular Sciences (CN), University of Chinese Academy of Sciences (CN)
Openalex Percentile: Top 0%
Organoboron and organosilicon chemistry
45.90
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