10.1248/cpb.c17-00391
The study presents a stereoselective method for the preparation of trans-(2S,6S)-Teneraic Acid, a naturally occurring imino acid with two asymmetric centers, using anodic oxidation and cobalt-catalyzed carbonylation. The key chemicals involved include methyl (S)-N-benzoyl-α-methoxypipecolate, which serves as a key intermediate in the synthesis, and dicobalt octacarbonyl [Co2(CO)8], acting as the catalyst precursor for the cobalt-catalyzed carbonylation step. The process aims to obtain trans-(2S,6S)-Teneraic Acid with high optical purity and yield, confirming its stereochemistry by comparing it with known isomers. The study also discusses the potential mechanisms behind the stereoselective carbonylation and provides detailed characterization of the synthesized Teneraic Acid.
10.1016/0022-328X(89)87352-8
The research explores a new route to synthesize seleno and telluro esters by carbonylating diaryl diselenides and ditellurides with carbon monoxide (CO) using Co2(CO)8 as a catalyst. The purpose is to develop a method that utilizes CO as a carbonyl source, which had not been done before. The study found that Co2(CO)8 is the most effective catalyst for this reaction, and the reactivity of the starting compounds follows the order Te > Se > S. The carbonylation of diaryl diselenides is catalytic in Co2(CO)8 in the presence of triphenylphosphine, which traps elemental selenium released during the reaction. The study concludes that while the method is effective for diselenides, it is less so for ditellurides due to the instability of the resulting telluro esters and the deactivation of the cobalt catalyst by liberated tellurium. Key chemicals used include diaryl diselenides and ditellurides, carbon monoxide, Co2(CO)8, and triphenylphosphine.