Chiral Autoamplification Meets Dynamic Chirality Control to Suggest Nonautocatalytic Chemical Model of Prebiotic Chirality Amplification

Chiral Autoamplification Meets Dynamic Chirality Control to Suggest Nonautocatalytic Chemical Model of Prebiotic Chirality Amplification Full article

Journal

Research
ISSN: 2639-5274

Output data

Year: 2019, Volume: 2019, Article number : UNSP 4756025, Pages count : DOI: 10.34133/2019/4756025

Authors

Talsi Evgenii P. ^1,2 , Bryliakova Anna A. ² , Ottenbacher Roman V. ^1,2 , Rybalova Tatyana V. ^1,3 , Bryliakov Konstantin P. ^1,2

Affiliations

1	(Данные Web of science) Novosibirsk State Univ, Pirogova 2, Novosibirsk 630090, Russia
2	(Данные Web of science) Boreskov Inst Catalysis, Pr Lavrentieva 5, Novosibirsk 630090, Russia
3	(Данные Web of science) Vorozhtsov Novosibirsk Inst Organ Chem, Pr Lavrentieva 9, Novosibirsk 630090, Russia

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.

Talsi E.P. , Bryliakova A.A. , Ottenbacher R.V. , Rybalova T.V. , Bryliakov K.P.
Chiral Autoamplification Meets Dynamic Chirality Control to Suggest Nonautocatalytic Chemical Model of Prebiotic Chirality Amplification

Research. 2019. V.2019. UNSP 4756025 . DOI: 10.34133/2019/4756025 WOS Scopus РИНЦ

Full text from publisher

Published print:

Nov 4, 2019

Web of science	WOS:000524980100048
Scopus	2-s2.0-85078782358
Elibrary	43244809
OpenAlex	W2988205493