中文版 | English
Title

Palladium catalyzed decarboxylative beta-C-glycosylation of glycals with oxazol-5-(4H)-ones as acceptors

Author
Corresponding AuthorYao, Hui; Xiang, Shao-Hua
Publication Years
2022-10-01
DOI
Source Title
ISSN
2052-4129
Abstract
Despite the increased importance of C-glycosides in biochemistry, the strategy for creating the C-glycosidic bond stereoselectively has received less attention than that for its O- and N-counterparts. We describe here a beta-C-glycosylation of oxazol-5(4H)-ones which are the direct precursors of amino acids. For a wide variety of glycal donors and glycosyl acceptors, this chemistry could be accomplished with excellent efficiency and exquisite chemoselectivity without exogenous bases in most cases. The excellent stereocontrol at the anomeric center originates from the steric hindrance imposed by the bulky phosphine ligand.
URL[Source Record]
Indexed By
SCI ; EI
Language
English
SUSTech Authorship
First ; Corresponding
Funding Project
Shenzhen Special Funds[JCYJ20180305123508258]
WOS Research Area
Chemistry
WOS Subject
Chemistry, Organic
WOS Accession No
WOS:000866135000001
Publisher
EI Accession Number
20224513055932
EI Keywords
Ligands ; Palladium ; Phosphorus compounds
ESI Classification Code
Biology:461.9 ; Precious Metals:547.1 ; Biochemistry:801.2 ; Physical Chemistry:801.4
Data Source
Web of Science
Citation statistics
Cited Times [WOS]:2
Document TypeJournal Article
Identifierhttp://kc.sustech.edu.cn/handle/2SGJ60CL/406550
DepartmentShenzhen Grubbs Institute
理学院_化学系
Affiliation
1.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China
2.Southern Univ Sci & Technol, Dept Chem, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Peoples R China
3.China Three Gorges Univ, Coll Biol & Pharmaceut Sci, Hubei Key Lab Nat Prod Res & Dev, Yichang 443002, Peoples R China
First Author AffilicationShenzhen Grubbs Institute;  Department of Chemistry
Corresponding Author AffilicationShenzhen Grubbs Institute;  Department of Chemistry
First Author's First AffilicationShenzhen Grubbs Institute
Recommended Citation
GB/T 7714
Ding, Wei-Yi,Liu, Huan-Huan,Cheng, Jun Kee,et al. Palladium catalyzed decarboxylative beta-C-glycosylation of glycals with oxazol-5-(4H)-ones as acceptors[J]. Organic Chemistry Frontiers,2022.
APA
Ding, Wei-Yi,Liu, Huan-Huan,Cheng, Jun Kee,Yao, Hui,Xiang, Shao-Hua,&Tan, Bin.(2022).Palladium catalyzed decarboxylative beta-C-glycosylation of glycals with oxazol-5-(4H)-ones as acceptors.Organic Chemistry Frontiers.
MLA
Ding, Wei-Yi,et al."Palladium catalyzed decarboxylative beta-C-glycosylation of glycals with oxazol-5-(4H)-ones as acceptors".Organic Chemistry Frontiers (2022).
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