Abstract: Oxidative kinetic resolution of 1-phenylethanol in the presence of manganese complexes, bearing conformationally non-rigid 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 (non-racemic) 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.

Cite: Talsi E.P. , Bryliakova A.A. , Ottenbacher R.V. , Rybalova T.V. , Bryliakov K.P.
Chiral Autoamplification Meets Dynamic Chirality Control to Suggest Non-Autocatalytic Chemical Model of Prebiotic Chirality Amplification
Research. 2019. V.2019. 4756025 :1-9. DOI: 10.34133/2019/4756025 WOS Scopus РИНЦ AN PMID OpenAlex

Files: Full text from publisher

Dates:

Submitted:	Jul 30, 2019
Accepted:	Sep 16, 2019
Published print:	Nov 4, 2019
Published online:	Nov 4, 2019

Identifiers:

Web of science:	WOS:000524980100048
Scopus:	2-s2.0-85078782358
Elibrary:	43244809
Chemical Abstracts:	2020:2203154
PMID:	31922134
OpenAlex:	W2988205493

Citing:

DB	Citing
Scopus	8
Web of science	7
Elibrary	8
OpenAlex	7

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