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Isolation of Sharpless reaction intermediates epoxidation and characterization of these species by theoretical calculations

Grant number: 15/11769-9
Support type:Scholarships in Brazil - Scientific Initiation
Effective date (Start): August 01, 2015
Effective date (End): November 30, 2016
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Physical-Chemistry
Principal Investigator:Thiago Carita Correra
Grantee:André Santos Fernandes
Home Institution: Instituto de Química (IQ). Universidade de São Paulo (USP). São Paulo , SP, Brazil
Associated research grant:14/15962-5 - Reaction mechanism of asymmetric catalysts by mass spectrometry and gas-phase vibrational ion spectroscopy, AP.JP
Associated scholarship(s):15/22811-6 - Characterization of Sharpless reaction intermediates by IRMPD spectroscopy at CLIO free-electron laser facility, BE.EP.IC


The core of this project lies in the study of the titanium tetrapropoxide/tartrate catalytic system, which is applied for the Sharpless asymmetric epoxidation, exceedingly important in synthetic chemistry. This system was chosen due to the uncertainties about the nature of effective catalytic structure, that controls the asymmetric oxidation of allyl alcohols. Taking into account that this study will be made, experimentally, by means of vibrational ion spectroscopy (IRMPD), the goal of the scholarship is to determine, in a systematic manner, the optimal conditions for the formation of ions of interest and the subsequent extraction of reactive intermediates by soft ionization methods (electrospray). Meanwhile, electronic structure calculation will be performed aiming the comparison with the spectroscopic results, as well as assistance in their acquisition. It is worth mentioning that the IRMPD vibrational spectroscopic experiments at the fingerprint region are already approved to be carried out in CLIO free electron laser in Orsay, France. Moreover, Philippe Maître, the director of CLIO, has shown interest in receiving the recipient of this scholarship for a longer period.

Scientific publications
(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)
FERNANDES, ANDRE SANTOS; MAITRE, PHILIPPE; CORRERA, THIAGO CARITA. Evaluation of the Katsuki-Sharpless Epoxidation Precatalysts by ESI-FTMS, CID, and IRMPD Spectroscopy. Journal of Physical Chemistry A, v. 123, n. 5, p. 1022-1029, FEB 7 2019. Web of Science Citations: 1.
CORRERA, THIAGO CARITA; FERNANDES, ANDRE SANTOS; REGINATO, MARCELO MOTA; DUCATI, LUCAS COLUCCI; BERDEN, GIEL; OOMENS, JOS. Probing the geometry reorganization from solution to gas-phase in putrescine derivatives by IRMPD, H-1-NMR and theoretical calculations. Physical Chemistry Chemical Physics, v. 19, n. 35, p. 24330-24340, SEP 21 2017. Web of Science Citations: 4.
BARBEIRO, CRISTIANE S.; VASCONCELOS, STANLEY N. S.; ZUKERMAN-SCHPECTOR, JULIO; CARACELLI, IGNEZ; PIMENTA, DANIEL C.; RODRIGUES, ANA CLARA B.; FERNANDES, ANDRE S.; CORRERA, THIAGO C.; BASTOS, ERICK L.; STEFANI, HELIO A. Chlorinated 2-hydroxynaphthalenoxazolines: Synthesis, Reaction Mechanism and Fluorescence Properties. CHEMISTRYSELECT, v. 1, n. 18, p. 5647-5652, NOV 1 2016. Web of Science Citations: 5.

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