NOVOCAT · Tha novo catalytic synthesis of β-aminoacids from CO2

Tha novo catalytic synthesis of β-aminoacids from CO2

Given the non-toxicity and natural-abundance of CO2, it comes as no surprise that chemists have been challenged to design catalytic technologies that harness its potential as C1 synthon for synthetic applications. Among various scenarios, the conversion of CO2 into carboxylic acids constitutes an ideal target for CO2 sequestration since these compounds are fundamental units in organic syntheses as well as being privileged motifs in many pharmaceuticals. In recent years, the Martin group has pioneered the development of metal-catalyzed reductive carboxylation protocols using simple and commercially available organic halides or pseudohalides as coupling partners with CO2. Albeit significant advances have been achieved, the scope of these protocols is still rather narrow and rather substrate-dependent. Prompted by the utmost synthetic and societal relevance of amino acids, key structural units of proteins and compounds that display important biological activities (Figure 1), the means to convert ubiquitous CO2 into valuable amino acids in a catalytic endeavor would be particularly appreciated. as well as their unique role for our society. With such premise in hand, NOVOCAT aimed at the development of a catalytic platform for preparing β-amino acids via direct carboxylation of widely accessible aziridines with CO2. The objectives were the following: - To prepare well-defined metal intermediates via C-N bond-cleavage of aziridines; - To design a catalytic reductive carboxylation of aziridines via synergistic C-N bond cleavage / CO2 insertion event, even in an asymmetric fashion; - To apply the know-how for the synthesis of natural products Despite extensive investigations, little success was achieved and the viability of obtaining amino acids from CO2 following the premises of NOVOCAT were not fully assessed. During our investigations with CO2, a serendipitous reaction was observed when using silylboranes as mediators for CO2 insertion in the presence of fluorine-containing molecules. Control experiments revealed that a C–F silylation event occurs with great efficiency, an aspect that could be extended to a wide number of compounds analyzed, including within the context of late-stage functionalization.

Текст от CORDIS, на английски · Данни: CORDIS, © Европейски съюз