Expedient asymmetric synthesis of (2S,3S)-Boc-phenylalanine epoxide,a key intermediate for the synthesis of biologically active compounds |
| |
Authors: | Ramón Badorrey María D Díaz-de-Villegas José A Gálvez |
| |
Institution: | Departamento de Química Orgánica, Instituto de Ciencia de Materiales de Aragón, Instituto Universitario de Catálisis Homogénea, Universidad de Zaragoza-CSIC, E-50009 Zaragoza, Spain |
| |
Abstract: | The asymmetric synthesis of (2S,3S)-3-(tert-butoxycarbonyl)amino-1,2-epoxy-4-phenylbutane (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·OEt2 as an imine precomplexing agent. |
| |
Keywords: | |
本文献已被 ScienceDirect 等数据库收录! |
|