Autoamplification-Enhanced Oxidative Kinetic Resolution of sec-Alcohols and Alkyl Mandelates, and its Kinetic Model

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Autoamplification-Enhanced Oxidative Kinetic Resolution of sec-Alcohols and Alkyl Mandelates, and its Kinetic Model. / Talsi, Evgenii P.; Bryliakov, Konstantin P.

In: ChemCatChem, Vol. 10, No. 12, 21.06.2018, p. 2693-2699.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{04494a251db042a99bd4a6ee5de44c3f,

title = "Autoamplification-Enhanced Oxidative Kinetic Resolution of sec-Alcohols and Alkyl Mandelates, and its Kinetic Model",

abstract = "In this contribution, the new dynamic nonlinear effect in asymmetric catalysis is discussed, manifesting itself in the oxidative kinetic resolution (OKR) of racemic secondary benzylic alcohols and alkyl mandelates with H2O2 in the presence of chiral Mn-based catalyst, with the apparent selectivity factor (krel) of the resolution being nonconstant over the reaction course. Typically, the initial growth of krel is changed into decay at high conversions. In this contribution, we demonstrate the oxidative kinetic resolution of various substrates bearing sec-alcoholic moieties, with the krel varying in different manners with increasing substrate conversion. We also present the predictive kinetic model of OKR with participation of asymmetric autoamplification. The influence of substrate and catalyst structure, as well as solvents and additives, on the behavior of krel variation, is discussed.",

keywords = "asymmetric autoamplification, chirality, hydrogen peroxide, kinetic resolution, manganese",

author = "Talsi, {Evgenii P.} and Bryliakov, {Konstantin P.}",

note = "Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2018",

month = jun,

day = "21",

doi = "10.1002/cctc.201800180",

language = "English",

volume = "10",

pages = "2693--2699",

journal = "ChemCatChem",

issn = "1867-3880",

publisher = "Wiley - VCH Verlag GmbH & CO. KGaA",

number = "12",

}

RIS

TY - JOUR

T1 - Autoamplification-Enhanced Oxidative Kinetic Resolution of sec-Alcohols and Alkyl Mandelates, and its Kinetic Model

AU - Talsi, Evgenii P.

AU - Bryliakov, Konstantin P.

PY - 2018/6/21

Y1 - 2018/6/21

N2 - In this contribution, the new dynamic nonlinear effect in asymmetric catalysis is discussed, manifesting itself in the oxidative kinetic resolution (OKR) of racemic secondary benzylic alcohols and alkyl mandelates with H2O2 in the presence of chiral Mn-based catalyst, with the apparent selectivity factor (krel) of the resolution being nonconstant over the reaction course. Typically, the initial growth of krel is changed into decay at high conversions. In this contribution, we demonstrate the oxidative kinetic resolution of various substrates bearing sec-alcoholic moieties, with the krel varying in different manners with increasing substrate conversion. We also present the predictive kinetic model of OKR with participation of asymmetric autoamplification. The influence of substrate and catalyst structure, as well as solvents and additives, on the behavior of krel variation, is discussed.

AB - In this contribution, the new dynamic nonlinear effect in asymmetric catalysis is discussed, manifesting itself in the oxidative kinetic resolution (OKR) of racemic secondary benzylic alcohols and alkyl mandelates with H2O2 in the presence of chiral Mn-based catalyst, with the apparent selectivity factor (krel) of the resolution being nonconstant over the reaction course. Typically, the initial growth of krel is changed into decay at high conversions. In this contribution, we demonstrate the oxidative kinetic resolution of various substrates bearing sec-alcoholic moieties, with the krel varying in different manners with increasing substrate conversion. We also present the predictive kinetic model of OKR with participation of asymmetric autoamplification. The influence of substrate and catalyst structure, as well as solvents and additives, on the behavior of krel variation, is discussed.

KW - asymmetric autoamplification

KW - chirality

KW - hydrogen peroxide

KW - kinetic resolution

KW - manganese

UR - http://www.scopus.com/inward/record.url?scp=85048155149&partnerID=8YFLogxK

U2 - 10.1002/cctc.201800180

DO - 10.1002/cctc.201800180

M3 - Article

AN - SCOPUS:85048155149

VL - 10

SP - 2693

EP - 2699

JO - ChemCatChem

JF - ChemCatChem

SN - 1867-3880

IS - 12

ER -

ID: 14154974