Oxidant-controlled heck-type C-glycosylation of glycals with arylboronic acids: stereoselective synthesis of aryl 2-deoxy-C-glycosides.
Oxidative Heck-type C-glycosylations of glycals with various arylboronic acids using Pd(OAc)(2) as catalyst in the presence of oxidant were developed. The corresponding ketone, enol ether, and enone types of C-glycosides were predictably obtained with benzoquinone (BQ), Cu(OAc)(2)/O(2), and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidants, respectively. This method provides a simple, mild, and stereoselective synthesis of aryl 2-deoxy-C-glycosides.
Xiong
De-Cai
DC
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, and School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd No. 38, Beijing 100191, China.
Zhang
Li-He
LH
Ye
Xin-Shan
XS
D016227:Benzoquinones / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004988:Ethers, Cyclic / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D016877:Oxidants / Q000737:chemistry; D013237:Stereoisomerism
D016227:Benzoquinones; D001897:Boronic Acids; D004988:Ethers, Cyclic; D006027:Glycosides; D016877:Oxidants; C000928:dichlorodicyanobenzoquinone