Dynamic kinetic resolution of epichlorohydrin via enantioselective catalytic ring opening with TMSN3. Practical synthesis of aryl oxazolidinone antibacterial agents

Article abstract of DOI:10.1016/0040-4039(96)01835-7

The dynamic kinetic resolution of racemic epichlorohydrin has been achieved via enantioselective asymmetric ring opening with TMSN₃ catalyzed by the (salen)Cr(III)N₃ complex 1. The resulting 3-azido-1-chloro-2-trimethylsiloxypropane product was obtained in high enantiomeric purity and incorporated into the synthesis of U-100592, a representative from a class of highly-promising aryl oxazolidinone antibacterial agents.