beta-C-Glycosylation with 2-Oxindole Acceptors via Palladium- Reactions

Ding, Wei-Yi1; Zhao, Hao-Wen1; Cheng, Jun Kee1; Lu, Zhiqiang2; Xiang, Shao-Hua1; Tan, Bin1

2022-09-01

10.1021/acs.orglett.2c02881

ORGANIC LETTERS   影响因子和分区

1523-7060

1523-7052

This report describes a highly efficient beta-selective C-glycosylation of bicyclic galactals with 2-oxindoles through a palladium-catalyzed decarboxylative pathway. A variety of sub-strates representing both glycosyl donors and acceptors could be transformed in greater than 90% yields under mild reaction conditions. The decarboxylation intermediate of galactal could serve as an efficient base to deprotonate the enol tautomer of 2-oxindole and enhance its nucleophilicity. The beta-selective nucleophilic addition at the anomeric center originates from the steric hindrance imposed by the palladium and bulky ligand.

SCI

英语

NI论文

第一 ; 通讯

Shenzhen Special Funds[JCYJ20180305123508258]

Chemistry

Chemistry, Organic

WOS:000861273400001

AMER CHEMICAL SOC

CHEMISTRY

Web of Science

1.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Peoples R China
2.Luoyang Normal Univ, Coll Chem & Chem Engn, Henan Key Lab Funct Oriented Porous Mat, Luoyang 471934, Peoples R China

Ding, Wei-Yi,Zhao, Hao-Wen,Cheng, Jun Kee,et al. beta-C-Glycosylation with 2-Oxindole Acceptors via Palladium- Reactions[J]. ORGANIC LETTERS,2022.

Ding, Wei-Yi,Zhao, Hao-Wen,Cheng, Jun Kee,Lu, Zhiqiang,Xiang, Shao-Hua,&Tan, Bin.(2022).beta-C-Glycosylation with 2-Oxindole Acceptors via Palladium- Reactions.ORGANIC LETTERS.

Ding, Wei-Yi,et al."beta-C-Glycosylation with 2-Oxindole Acceptors via Palladium- Reactions".ORGANIC LETTERS (2022).