Amino, Yusuke’s team published research in Chemical & Pharmaceutical Bulletin in 2017 | CAS: 59234-40-1

Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1) is a member of piperidine. Piperidine-containing compounds are also frequently employed in synthesis as ligands or auxiliaries. Accordingly, many efforts have been devoted to the development of novel methods for the synthesis of these compounds over the years.SDS of cas: 59234-40-1

SDS of cas: 59234-40-1On September 30, 2017 ,《Stereo-selective preparation of teneraic acid, trans-(2S,6S)-piperidine-2,6-dicarboxylic acid, via anodic oxidation and cobalt-catalyzed carbonylation》 was published in Chemical & Pharmaceutical Bulletin. The article was written by Amino, Yusuke; Nishi, Seiichi; Izawa, Kunisuke. The article contains the following contents:

Teneraic acid (piperidine-2,6-dicarboxylic acid) is a naturally occurring imino acid that comprises of three stereoisomers due to its two asym. centers at C2 and C6. The configuration of natural teneraic acid is reported to correspond to trans-(2S,6S). However, a few studies are focused on the stereospecific synthesis of trans-(2S,6S)-teneraic acid. The present study investigates a convenient synthetic method that includes regiospecific anodic oxidation and stereospecific cobalt-catalyzed carbonylation to obtain trans-(2S,6S)-teneraic acid. Me (S)-N-benzoyl-α-methoxypipecolate, the key intermediate that displays a structure that corresponds to an intermediate (N-α-hydroxyalkyl amide) of intramol. amidocarbonylation, was obtained via an anodic oxidation of Me (S)-N-benzoylpipecolate. Subsequently, cobalt-catalyzed carbonylation converted the Me (S)-N-benzoyl-α-methoxypipecolate to trans-(2S,6S)-N-benzoyl-teneraic acid di-Me ester in good optical purity (>95% enantiomeric excess (ee)) and modest yield (63%). Finally, de-protection occurred via acidic hydrolysis to obtain trans-(2S,6S)-teneraic acid. The stereochem. of synthesized teneraic acid was confirmed as corresponding to trans-(2S,6S) by comparing its phys. properties with those of a cis-meso-isomer and those of a trans-(2S,6S)-isomer that were reported in previous studies. In the experiment, the researchers used Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1SDS of cas: 59234-40-1)

Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1) is a member of piperidine. Piperidine-containing compounds are also frequently employed in synthesis as ligands or auxiliaries. Accordingly, many efforts have been devoted to the development of novel methods for the synthesis of these compounds over the years.SDS of cas: 59234-40-1

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem