Journal
CHEMICAL COMMUNICATIONS
Volume 57, Issue 48, Pages 5953-5956Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1cc00496d
Keywords
-
Categories
Funding
- National Science Foundation [CHE-1847813]
- American Chemical Society Petroleum Research Fund
Ask authors/readers for more resources
The cleavage of alkyl ethers by hydrosilylation is demonstrated with stability of O-aryl glycosides under iridium- and borane-catalyzed conditions. A cationic bis(phosphine)iridium complex catalyzes the selective 3-demethylation of various 2,3,4-tri-O-methyl pyranoses.
The cleavage of alkyl ethers by hydrosilylation is a powerful synthetic tool for the generation of silyl ethers. Previous attempts to apply this transformation to carbohydrate derivatives have been constrained by poor selectivity and preferential reduction of the anomeric position. O-Aryl glycosides are found to be stable under iridium- and borane-catalyzed hydrosilylation conditions, allowing for alkyl ether cleavage without loss of anomeric functionality. A cationic bis(phosphine)iridium complex catalyzes the selective 3-demethylation of a variety of 2,3,4-tri-O-methyl pyranoses, offering a unique approach to 3-hydroxy or 3-acetyl 2,4-di-O-methylpyranoses.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available