A Mechanistic Investigation of the Kinetic Resolution of Secondary Aromatic Alcohols Using a Ferrocene-Based Planar Chiral 4-(Dimethylamino)pyridine Catalyst
2015 (English)In: CHEMISTRY-A EUROPEAN JOURNAL, ISSN 0947-6539, Vol. 21, no 14, 5623-5631 p.Article in journal (Refereed) Published
A detailed kinetic analysis for the acetylation of 1-phenylethanol with acetic anhydride catalyzed by the planar chiral DMAP catalyst (–)-1 is presented. The study include a computational investigation of the potential energy surface including the rate-limiting and stereoselective transitionstates at the DFT level of theory. The kinetic study suggests that the reaction proceeds with first order in catalyst and in 1-phenylethanol, while the acetic anhydride shows a fractional order. The fractional order is racionalized based on an equilibrium between the free and the acetylated catalyst.
Place, publisher, year, edition, pages
2015. Vol. 21, no 14, 5623-5631 p.
Reaction progress kinetic analysis, DFT calculation
IdentifiersURN: urn:nbn:se:uu:diva-233714DOI: 10.1002/chem.201405793ISI: 000352504500041PubMedID: 25677932OAI: oai:DiVA.org:uu-233714DiVA: diva2:753955