Systems Chemistry: Kinetic and Computational Analysis of a Nearly Exponential Organic Replicator

✍ Scribed by Maik Kindermann; Insa Stahl; Malte Reimold; Wolf Matthias Pankau; Günter von Kiedrowski

• Publisher: John Wiley and Sons
• Year: 2005
• Tongue: English
• Weight: 272 KB
• Volume: 44
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.200501527

✦ Synopsis

In 1997, Wang and Sutherland reported a case of selfreplication in a Diels-Alder reaction. [1] This system is remarkable for at least two reasons: it constituted the first example of nearly exponential growth and it had the potential to exhibit two kinds of self-replication, homochiral autocatalysis and heterochiral cross-catalysis, because a chiral diene was employed. Unfortunately, the authors could not complete a stereochemical analysis of their system. We report herein mechanistic and stereochemical studies of variants of the Wang-Sutherland replicator. We show that only one of four potential diastereomers is formed within our detection limits and that this diastereomer is involved in both autocatalytic and cross-catalytic channels. A computational study suggests that the system can be classified as an example of a nearby [*] Dr.