期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 40, 页码 14115-14119出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201907129
关键词
Bronsted acid catalysis; carbohydrates; glycosylation; organocatalysis
资金
- JSPS KAKENHI [16H06384, 17K15423]
- Takeda Science Foundation
- JSPS
- Grants-in-Aid for Scientific Research [16H06384, 17K15423] Funding Source: KAKEN
The direct 2-deoxyglycosylation of nucleophiles with glycals leads to biologically and pharmacologically important 2-deoxysugar compounds. Although the direct addition of hydroxyl and sulfonamide groups have been well developed, the direct 2-deoxyglycosylation of amide groups has not been reported to date. Herein, we show the first direct 2-deoxyglycosylation of amide groups using a newly designed Bronsted acid catalyst under mild conditions. Through mechanistic investigations, we discovered that the amide group can inhibit acid catalysts, and the inhibition has made the 2-deoxyglycosylation reaction difficult. Diffusion-ordered two-dimensional NMR spectroscopy analysis implied that the 2-chloroazolium salt catalyst was less likely to form aggregates with amides in comparison to other acid catalysts. The chlorine atom and the extended pi-scaffold of the catalyst played a crucial role for this phenomenon. This relative insusceptibility to inhibition by amides is more responsible for the catalytic activity than the strength of the acidity.
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