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A convenient and high yield method to prepare 4-hydroxypyroglutamic acids

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
42
Issue
32
Identifiers
DOI: 10.1016/s0040-4039(01)01030-9
Keywords
  • 4-Hydroxyl Pyroglutamic Acid
  • Ruthenium Dioxide
  • Oxidation
  • Mitsunobu Reaction
  • N-Acyliminium Ion

Abstract

Abstract RuO 2/NaIO 4 oxidation of N-Boc-4-silyloxy and 4-acetoxy proline methyl esters under ethyl acetate/water biphase condition gave N-Boc-4-silyloxy and 4-acetoxy pyroglutamic acid derivatives in high yields. Desilylation with TBAF afforded both cis- and trans- N-Boc-methyl-4-hydroxy pyroglutamates.

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