%0 Journal Article
%T Organoautocatalysis: Challenges for experiment and theory
%A Svetlana B Tsogoeva
%J Journal of Systems Chemistry
%D 2010
%I BioMed Central
%R 10.1186/1759-2208-1-8
%X The idea that molecules could make countless exact copies of themselves offers fascinating prospects in materials science and holds interesting implications for the origin of life on earth. Oparin was the first to realize the importance of self-replication for life processes [1,2]. Self-replication appeared for a long time to be a sole domain of RNA and DNA molecules replicating via enzymatic pathways [3], until the pioneering studies of von Kiedrowski [4-7], who first demonstrated that oligonucleotides could self-replicate even non-enzymatically via template-directed autocatalysis. Self-replication has been also invoked as an integral part of systems chemistry [8,9].That even much smaller and simpler molecules are capable of exhibiting self-replication, was first shown by Rebek and co-workers for artificial synthetic models (Figure 1) [10,11].The finding has been much debated. Challenged by Menger et al. [12,13], who argued that the rate enhancement is due to amide-catalysis and not due to template-autocatalysis, Rebek's interpretation of self-replication has been vindicated by Reinhoudt's group later [14]. Since then, a few other scattered reports about self-replicating molecules have appeared in the literature [15-18].The potential enantioselectivity of the self-replicating autocatalytic process was implied, but has not drawn particular attention at that time.Asymmetric autocatalysis, a term first introduced by Wynberg, is the process of automultiplication of a chiral compound in which the chiral product acts as a chiral catalyst for its own formation [19]. Catalyst and product possess of the same absolute configuration and are structurally related. The first example for such a process was reported by Soai in 1990, in the irreversible enantioselective addition of dialkylzinc reagents to pyridine-3-carbaldehyde (Figure 2) [20]. Thus, when product of the reaction was used as catalyst at 20 mol% loading and with 86% ee, the newly generated product was isolated in 67
%U http://www.jsystchem.com/content/1/1/8