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- Title
Autoamplification‐Enhanced Oxidative Kinetic Resolution of sec‐Alcohols and Alkyl Mandelates, and its Kinetic Model.
- Authors
Talsi, Evgenii P.; Bryliakov, Konstantin P.
- Abstract
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.
- Subjects
BENZYL alcohol; KINETIC resolution; BIOMIMETIC chemicals; AMINOPYRIDINES; AUTOCATALYSIS; CHEMICAL kinetics
- Publication
ChemCatChem, 2018, Vol 10, Issue 12, p2693
- ISSN
1867-3880
- Publication type
Article
- DOI
10.1002/cctc.201800180