An efficient synthesis of (-)-chloramphenicol via asymmetric catalytic aziridination: a comparison of catalysts prepared from triphenylborate and various linear and vaulted biaryls.

Abstract

[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.