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Open-Air Stereoselective Construction of C-Aryl Glycosides
- Source :
- Organic Letters. 22:1144-1148
- Publication Year :
- 2020
- Publisher :
- American Chemical Society (ACS), 2020.
-
Abstract
- A new methodology of stereoselective C-glycosylation has been developed with 3,4-O-carbonate glycals and boronic acids, catalyzed by 1,2-bis(phenylsulfinyl)ethane palladium(II) acetate under open-air conditions at room temperature. This mild method is simple in operation, wide in substrate range, and tolerant in alcoholic/phenolic hydroxyl and amino groups. High to excellent yields were observed for all substrates tested, with the driving force mainly contributed by decarboxylation. Meanwhile, the high 1,4-trans-selectivity was achieved by steric effects as proposed.
- Subjects :
- Steric effects
010405 organic chemistry
Decarboxylation
Aryl
Organic Chemistry
chemistry.chemical_element
Substrate (chemistry)
Stereoisomerism
010402 general chemistry
01 natural sciences
Biochemistry
0104 chemical sciences
Catalysis
chemistry.chemical_compound
chemistry
Organic chemistry
Stereoselectivity
Physical and Theoretical Chemistry
Palladium
Subjects
Details
- ISSN :
- 15237052 and 15237060
- Volume :
- 22
- Database :
- OpenAIRE
- Journal :
- Organic Letters
- Accession number :
- edsair.doi...........ed54b2fd0d1bd46d19008aec18f08218