Highly stereoselective synthesis of aminoglycosides via rhodium-catalyzed and substrate-controlled aziridination of glycals.
The flexible installations of a sulfamate ester on a glycal scaffold at C3, C4, or C6 approaching alpha- or beta-aminoglycosides is communicated. A variety of glycal acceptors (O, S, and N) were applied, enhancing the utility of this method as an operationally simple protocol for the stereoselective synthesis of polyfunctionalized alpha- or beta- aminosaccharides.
Lorpitthaya
Rujee
R
Division of Chemical and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
Sophy
K B
KB
Kuo
Jer-Lai
JL
Liu
Xue-Wei
XW
D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry; D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D000617:Aminoglycosides; D001388:Aziridines; D006027:Glycosides; D012238:Rhodium