An efficient synthesis of (-)-chloramphenicol via asymmetric catalytic aziridination: a comparison of catalysts prepared from triphenylborate and various linear and vaulted biaryls.
[reaction--see text] The antibiotic (-)-choramphenicol has been synthesized in only four steps from p-nitro-benzaldehyde in optically pure form from an asymmetric catalytic aziridination reaction with a chiral catalyst prepared from triphenylborate and the (R)-VAPOL ligand. Catalysts generated from the VAPOL and VANOL ligands give much higher asymmetric induction than do catalysts prepared from 6,6'-diphenylVAPOL, BINOL, and BANOL ligands.
Loncaric
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Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.
Wulff
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WD
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D001388:Aziridines / Q000138:chemical synthesis*; D001881:Borates; D002384:Catalysis; D002701:Chloramphenicol / Q000138:chemical synthesis*; D011084:Polycyclic Aromatic Hydrocarbons; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D001388:Aziridines; D001881:Borates; D011084:Polycyclic Aromatic Hydrocarbons; D002701:Chloramphenicol