In Situ Mass Spectrometric and Kinetic Investigations of Soai's Asymmetric Autocatalysis.

ABSTRACT: Chemical reactions that lead to a spontaneous symmetry breaking or amplification of the enantiomeric excess are of fundamental interest in explaining the formation of a homochiral world. An outstanding example is Soai's asymmetric autocatalysis, in which small enantiomeric excesses of the added product alcohol are amplified in the reaction of diisopropylzinc and pyrimidine-5-carbaldehydes. The exact mechanism is still in dispute due to complex reaction equilibria and elusive intermediates. In situ high-resolution mass spectrometric measurements, detailed kinetic analyses and doping with in situ reacting reaction mixtures show the transient formation of hemiacetal complexes, which can establish an autocatalytic cycle. We propose a mechanism that explains the autocatalytic amplification invo

SUBMITTER: Trapp O 

PROVIDER: S-EPMC7756584 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature