Asymmetric synthesis of N-protected syn and anti (E)-3-amino-2-hydroxy-4-hexenoate: A practical method for the C-alpha epimerization of anti beta-amino-alpha-hydroxy acids

Journal article

A practical method to convert anti β-amino-α-hydroxy acids into the corresponding syn esters via the DCC/DMAP-HCl mediated esterification was devised, and methyl (2R,3S)-(E)-3-t-butoxycarbonylamino-2-hydroxy-4-hexenoate 15 was synthesised from the corresponding (2S,3S)-isomer 9 using the epimerization procedure developed. The α- and β-stereogenic centres of 9 were constructed by the Michael addition of a homochiral lithium amide to t- butyl sorbate and subsequent oxidation of the enolate intermediate in one pot.

Authors: Brackenridge, I; Davies, S; Fenwick, DR; Ichihara, O; Polywka, M

• Publication status: Published
• Journal: TETRAHEDRON
• Volume: 55
• Issue: 2
• Pages: 533-540
• Publication date: 1999-01-08
• DOI: 10.1016/S0040-4020(98)01051-5
• ISSN: 0040-4020
• Language: English