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Title: Effects of Water Addition on a Catalytic Fluorination of Dienamine
Authors: Kuraoku, Daiki
Yonamine, Tsunaki
Koja, Genta
Yoshida, Norio
Arimitsu, Satoru
Higashi, Masahiro  kyouindb  KAKEN_id  orcid https://orcid.org/0000-0001-9829-389X (unconfirmed)
Author's alias: 東, 雅大
Keywords: water addition
dienamine
fluorination
3D-RISM-SCF
solvent effect
Issue Date: Oct-2019
Publisher: MDPI AG
Journal title: Molecules
Volume: 24
Issue: 19
Thesis number: 3428
Abstract: We investigate the effects of water addition on a highly stereocontrolled fluorination of dienamine generated by α-branched enals and 6′-hydroxy-9-amino-9-deoxy-epi-quinidine with N-fluorobenzenesulfonimide (NFSI) in the presence of Brønsted acid both experimentally and theoretically. It is experimentally found that water addition to organic solvent significantly shortens the reaction time whereas excessive water addition decreases the enantiomeric excess. The results calculated with three-dimensional reference interaction site model self-consistent field (3D-RISM-SCF) method are in good agreement with the experimental ones. It is revealed that the shortness of reaction time is caused by the reactant destabilization and that the decrease in enantiomeric excess is due to the difference of hydration free energy between two transition states.
Rights: © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
URI: http://hdl.handle.net/2433/245906
DOI(Published Version): 10.3390/molecules24193428
PubMed ID: 31546593
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