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

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