A modular approach to catalytic stereoselective synthesis of chiral 1,2-diols and 1,3-diols
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. Cata...
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2025-01-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-024-55744-3 |
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| author | Sheng Xu Yuanyuan Ping Yinyan Su Haoyun Guo Aowei Luo Wangqing Kong |
| author_facet | Sheng Xu Yuanyuan Ping Yinyan Su Haoyun Guo Aowei Luo Wangqing Kong |
| author_sort | Sheng Xu |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-003b30f8807b4c76921b1579c4ef52ca |
| institution | Kabale University |
| issn | 2041-1723 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj-art-003b30f8807b4c76921b1579c4ef52ca2025-01-05T12:37:05ZengNature PortfolioNature Communications2041-17232025-01-0116111410.1038/s41467-024-55744-3A modular approach to catalytic stereoselective synthesis of chiral 1,2-diols and 1,3-diolsSheng Xu0Yuanyuan Ping1Yinyan Su2Haoyun Guo3Aowei Luo4Wangqing Kong5The Institute for Advanced Studies and Hongyi Honor College, Wuhan UniversityThe Institute for Advanced Studies and Hongyi Honor College, Wuhan UniversityThe Institute for Advanced Studies and Hongyi Honor College, Wuhan UniversityThe Institute for Advanced Studies and Hongyi Honor College, Wuhan UniversityThe Institute for Advanced Studies and Hongyi Honor College, Wuhan UniversityThe Institute for Advanced Studies and Hongyi Honor College, Wuhan UniversityAbstract 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.https://doi.org/10.1038/s41467-024-55744-3 |
| spellingShingle | Sheng Xu Yuanyuan Ping Yinyan Su Haoyun Guo Aowei Luo Wangqing Kong A modular approach to catalytic stereoselective synthesis of chiral 1,2-diols and 1,3-diols Nature Communications |
| title | A modular approach to catalytic stereoselective synthesis of chiral 1,2-diols and 1,3-diols |
| title_full | A modular approach to catalytic stereoselective synthesis of chiral 1,2-diols and 1,3-diols |
| title_fullStr | A modular approach to catalytic stereoselective synthesis of chiral 1,2-diols and 1,3-diols |
| title_full_unstemmed | A modular approach to catalytic stereoselective synthesis of chiral 1,2-diols and 1,3-diols |
| title_short | A modular approach to catalytic stereoselective synthesis of chiral 1,2-diols and 1,3-diols |
| title_sort | modular approach to catalytic stereoselective synthesis of chiral 1 2 diols and 1 3 diols |
| url | https://doi.org/10.1038/s41467-024-55744-3 |
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