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A Mechanistic Investigation of the Kinetic Resolution of Secondary Aromatic Alcohols Using a Ferrocene-Based Planar Chiral 4-(Dimethylamino)pyridine Catalyst
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. (Dinér)
KTH, School of Chemical Science and Engineering (CHE), Chemistry. Uppsala University, Sweden.ORCID iD: 0000-0001-6782-6622
2015 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 21, no 14, 5623-5631 p.Article in journal (Refereed) Published
Abstract [en]

A detailed computational and kinetic analysis of the acetylation of 1-phenylethanol with acetic anhydride catalyzed by planar chiral 4-(dimethylamino) pyridine (DMAP) catalyst ( )-1 is presented. The study includes a computational investigation of the potential-energy surface including the acylation and stereoselective transition states at the DFT level of theory. Experimentally, the kinetic study shows that the reaction proceeds in a first-order manner in catalyst, whereas both substrates, acetic anhydride and 1-phenylethanol, show fractional order, which is in accordance with steady-state conditions. The fractional order depends on an equilibrium between the free catalyst and the acetylated catalyst.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2015. Vol. 21, no 14, 5623-5631 p.
Keyword [en]
acylation, chirality, density functional calculations, kinetics, nucleophilic addition
National Category
Chemical Sciences
URN: urn:nbn:se:kth:diva-166343DOI: 10.1002/chem.201405793ISI: 000352504500041PubMedID: 25677932ScopusID: 2-s2.0-84925127164OAI: diva2:810666
Swedish Research CouncilKnut and Alice Wallenberg Foundation

QC 20150508 QC 20160113

Available from: 2015-05-08 Created: 2015-05-07 Last updated: 2016-01-13Bibliographically approved

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