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Asymmetric synthesis ofN-protectedsynandanti(E)-3-amino-2-hydroxy-4-hexenoate: A practical method for the C-α epimerization ofantiβ-amino-α-hydroxy acids

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
55
Issue
2
Identifiers
DOI: 10.1016/s0040-4020(98)01051-5
Keywords
  • Article

Abstract

Abstract A practocal 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 (2 R,3 S)-( E)-3- t-butoxycarbonylamino-2-hydroxy-4-hexenoate 15 was synthesised from the corresponding (2 S,3 S)-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.

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