Practical synthesis of C -aryl glycosides via redox-neutral Borono–Catellani reaction
Herein, we describe a practical Borono–Catellani strategy for the efficient synthesis of C -aryl glycosides, with readily available arylboronic esters and glycosyl chlorides as the building blocks. It features mild reaction conditions, excellent diastereoselectivities, and good functional group tole...
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| Published in | Chemical communications (Cambridge, England) Vol. 61; no. 4; pp. 736 - 739 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
CAMBRIDGE
Royal Soc Chemistry
07.01.2025
Royal Society of Chemistry |
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| Abstract | Herein, we describe a practical Borono–Catellani strategy for the efficient synthesis of
C
-aryl glycosides, with readily available arylboronic esters and glycosyl chlorides as the building blocks. It features mild reaction conditions, excellent diastereoselectivities, and good functional group tolerance. A diverse array of highly decorated
C
-(hetero)aryl glycosides are obtained in a convergent and redox-neutral manner. |
|---|---|
| AbstractList | Herein, we describe a practical Borono–Catellani strategy for the efficient synthesis of
C
-aryl glycosides, with readily available arylboronic esters and glycosyl chlorides as the building blocks. It features mild reaction conditions, excellent diastereoselectivities, and good functional group tolerance. A diverse array of highly decorated
C
-(hetero)aryl glycosides are obtained in a convergent and redox-neutral manner. Herein, we describe a practical Borono-Catellani strategy for the efficient synthesis of -aryl glycosides, with readily available arylboronic esters and glycosyl chlorides as the building blocks. It features mild reaction conditions, excellent diastereoselectivities, and good functional group tolerance. A diverse array of highly decorated -(hetero)aryl glycosides are obtained in a convergent and redox-neutral manner. Herein, we describe a practical Borono-Catellani strategy for the efficient synthesis of C-aryl glycosides, with readily available arylboronic esters and glycosyl chlorides as the building blocks. It features mild reaction conditions, excellent diastereoselectivities, and good functional group tolerance. A diverse array of highly decorated C-(hetero)aryl glycosides are obtained in a convergent and redox-neutral manner.Herein, we describe a practical Borono-Catellani strategy for the efficient synthesis of C-aryl glycosides, with readily available arylboronic esters and glycosyl chlorides as the building blocks. It features mild reaction conditions, excellent diastereoselectivities, and good functional group tolerance. A diverse array of highly decorated C-(hetero)aryl glycosides are obtained in a convergent and redox-neutral manner. Herein, we describe a practical Borono-Catellani strategy for the efficient synthesis of C-aryl glycosides, with readily available arylboronic esters and glycosyl chlorides as the building blocks. It features mild reaction conditions, excellent diastereoselectivities, and good functional group tolerance. A diverse array of highly decorated C-(hetero)aryl glycosides are obtained in a convergent and redox-neutral manner. |
| Author | Cheng, Hong-Gang Xu, Dekang Li, Xia Zhou, Qianghui Cui, Ziyang Cao, Liming |
| Author_xml | – sequence: 1 givenname: Dekang surname: Xu fullname: Xu, Dekang organization: Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), Hubei Key Lab on Organic and Polymeric OptoElectronic Materials, College of Chemistry and Molecular Sciences and The Institute for Advanced Studies and TaiKang Center for Life and Medical Sciences, Wuhan University, 430072, Wuhan, China – sequence: 2 givenname: Xia surname: Li fullname: Li, Xia organization: Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), Hubei Key Lab on Organic and Polymeric OptoElectronic Materials, College of Chemistry and Molecular Sciences and The Institute for Advanced Studies and TaiKang Center for Life and Medical Sciences, Wuhan University, 430072, Wuhan, China – sequence: 3 givenname: Ziyang surname: Cui fullname: Cui, Ziyang organization: Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), Hubei Key Lab on Organic and Polymeric OptoElectronic Materials, College of Chemistry and Molecular Sciences and The Institute for Advanced Studies and TaiKang Center for Life and Medical Sciences, Wuhan University, 430072, Wuhan, China – sequence: 4 givenname: Liming surname: Cao fullname: Cao, Liming organization: Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), Hubei Key Lab on Organic and Polymeric OptoElectronic Materials, College of Chemistry and Molecular Sciences and The Institute for Advanced Studies and TaiKang Center for Life and Medical Sciences, Wuhan University, 430072, Wuhan, China – sequence: 5 givenname: Hong-Gang orcidid: 0000-0001-9585-9093 surname: Cheng fullname: Cheng, Hong-Gang organization: Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), Hubei Key Lab on Organic and Polymeric OptoElectronic Materials, College of Chemistry and Molecular Sciences and The Institute for Advanced Studies and TaiKang Center for Life and Medical Sciences, Wuhan University, 430072, Wuhan, China – sequence: 6 givenname: Qianghui orcidid: 0000-0002-8125-0380 surname: Zhou fullname: Zhou, Qianghui organization: Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), Hubei Key Lab on Organic and Polymeric OptoElectronic Materials, College of Chemistry and Molecular Sciences and The Institute for Advanced Studies and TaiKang Center for Life and Medical Sciences, Wuhan University, 430072, Wuhan, China |
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| Snippet | Herein, we describe a practical Borono–Catellani strategy for the efficient synthesis of
C
-aryl glycosides, with readily available arylboronic esters and... Herein, we describe a practical Borono-Catellani strategy for the efficient synthesis of C-aryl glycosides, with readily available arylboronic esters and... Herein, we describe a practical Borono-Catellani strategy for the efficient synthesis of -aryl glycosides, with readily available arylboronic esters and... Herein, we describe a practical Borono–Catellani strategy for the efficient synthesis of C-aryl glycosides, with readily available arylboronic esters and... |
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| SubjectTerms | Aromatic compounds Chemical synthesis Chemistry Chemistry, Multidisciplinary Esters Functional groups Glycosides Physical Sciences Science & Technology |
| Title | Practical synthesis of C -aryl glycosides via redox-neutral Borono–Catellani reaction |
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