Expedient asymmetric synthesis of (2S,3S)-Boc-phenylalanine epoxide, a key intermediate for the synthesis of biologically active compounds

摘要

The asymmetric synthesis of (2S,3S)-3-(tert-butoxycarbonyl)amino-1,2-epoxy-4-plienylbutane [(2S,3S)-Boc-phenylalanine epoxide] has been achieved in six steps and in 55% overall yield from the N-benzylimine derived from (R)-2,3-O-isopropylidene-glyceraldehyde. The required vic-aminodiol intermediate was obtained through a highly diastereoselective addition of benzylmagnesium chloride to the N-benzylimine in the presence of BF3 center dot OEt2 as an imine precomplexing agent.