Chiral autoamplification meets dynamic chirality control to suggest nonautocatalytic chemical model of prebiotic chirality amplification

Evgenii P. Talsi, Anna A. Bryliakova, Roman V. Ottenbacher, Tatyana V. Rybalova, Konstantin P. Bryliakov

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Oxidative kinetic resolution of 1-phenylethanol in the presence of manganese complexes, bearing conformationally nonrigid achiral bis-amine-bis-pyridine ligands, in the absence of any exogenous chiral additives, is reported. The only driving force for the chiral discrimination is the small initial enantiomeric imbalance of the scalemic (nonracemic) substrate: the latter dynamically controls the chirality of the catalyst, serving itself as the chiral auxiliary. In effect, the ee of 1-phenylethanol increases monotonously over the reaction course. This dynamic control of catalyst chirality by the substrate has been unprecedented; a consistent kinetic model for this process is presented. The reported catalyzed substrate self-enantioenrichment mechanism is discussed in relation to the problem of prebiotic chirality amplification.

Original languageEnglish
Article number4756025
Number of pages9
JournalResearch
Volume2019
DOIs
Publication statusPublished - 4 Nov 2019

Fingerprint

Dive into the research topics of 'Chiral autoamplification meets dynamic chirality control to suggest nonautocatalytic chemical model of prebiotic chirality amplification'. Together they form a unique fingerprint.

Cite this