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4-Amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylic acid (β-TOAC), the first spin-labelled, cyclic, chiral β-amino acid resolved in an enantiomerically pure state

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
44
Issue
16
Identifiers
DOI: 10.1016/s0040-4039(03)00572-0
Keywords
  • Chiral Nitroxides
  • Modified β-Amino Acids
  • Spin-Labelled Amino Acids

Abstract

Abstract Amination of 3-carboxymethyl-1-oxyl-2,2,6,6-tetramethyl-4-piperidone with ( R)-α-methylbenzylamine, NaBH 3CN reduction of the resulting enamine and removal of the chiral auxiliary from the separated diastereoisomers, led to enantiomerically pure (3 S,4 S) and (3 R,4 R) methyl 4-amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylates.

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