Stereocontrolled synthesis of fully functionalized D-glucosamine monosaccharides via a domino nitro-Michael/Henry reaction.
A diastereoselective domino nitro-Michael/Henry reaction involving a beta-hydroxyaldehyde and a nitroalkene provides direct access to fully functionalized D-glucosamine monosaccharides.
Adibekian
Alexander
A
Laboratory for Organic Chemistry, Swiss Federal Institute of Technology (ETH) Zürich, Wolfgang-Pauli-Str. 10, Zürich 8093, Switzerland.
Timmer
Mattie S M
MS
Stallforth
Pierre
P
van Rijn
Jimmy
J
Werz
Daniel B
DB
Seeberger
Peter H
PH
D000447:Aldehydes / Q000737:chemistry; D005944:Glucosamine / Q000737:chemistry*; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D009574:Nitro Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D000447:Aldehydes; D009005:Monosaccharides; D009574:Nitro Compounds; D005944:Glucosamine