A modular approach to catalytic stereoselective synthesis of chiral 1,2-diols and 1,3-diols

Sheng Xu, Yuanyuan Ping, Yinyan Su, Haoyun Guo, Aowei Luo and Wangqing Kong (wqkong@whu.edu.cn)
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Sheng Xu: Wuhan University
Yuanyuan Ping: Wuhan University
Yinyan Su: Wuhan University
Haoyun Guo: Wuhan University
Aowei Luo: Wuhan University
Wangqing Kong: Wuhan University

Nature Communications, 2025, vol. 16, issue 1, 1-14

Abstract: Abstract Optically pure 1,2-diols and 1,3-diols are the most privileged structural motifs, widely present in natural products, pharmaceuticals and chiral auxiliaries or ligands. However, their synthesis relies on the use of toxic or expensive metal catalysts or suffer from low regioselectivity. Catalytic asymmetric synthesis of optically pure 1,n-diols from bulk chemicals in a highly stereoselective and atom-economical manner remains a formidable challenge. Here, we disclose a versatile and modular method for the synthesis of enantioenriched 1,2-diols and 1,3-diols from the high-production-volume chemicals ethane-1,2-diol (MEG) and 1,3-propanediol (PDO), respectively. The key to success is to temporarily mask the diol group as an acetonide, which imparts selectivity to the key step of C(sp3)-H functionalization. Additionally, 1,n-diols containing two stereogenic centers are also prepared through diastereoselective C(sp3)-H functionalization. The late-stage functionalization of biological active compounds and the expedient synthesis of chiral ligands and pharmaceutically relevant molecules further highlight the synthetic potential of this protocol.

Date: 2025
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DOI: 10.1038/s41467-024-55744-3

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