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

✍ Scribed by Karen Wright; Marco Crisma; Claudio Toniolo; Roland Török; Antal Péter; Michel Wakselman; Jean-Paul Mazaleyrat

• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 149 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(03)00572-0

✦ Synopsis

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